Tortuga, makers of a popular backpack and other luggage items for serious city travel, operates as a fully distributed company spanning multiple countries. As a travel company, that's almost expected. As a company that manufactures and ships a physical product, it's a bit of a head turner.

Tortuga's customers are often digital nomads or urban backpackers, so the remote origin story makes a lot of sense. Travel companies lend themselves to remote teams (we've interviewed a few here at Pajamas over the years). But Tortuga also has to deal with the constraints of designing, manufacturing, warehousing, shipping, and supporting a line of real, tangible products. That adds a ton of extra complexity.

We talked to CEO Fred Perrotta about how the teams makes it all work.

What does Tortuga do and what do you do there?

Tortuga helps people live on their terms by making luggage for city travel. I'm the co-founder and CEO.

How many people are at the company now and how spread out are you?

We are a team of 9, based mostly in North America and China, where we manufacture.

What made you decide to start building Tortuga as a distributed company?

Becoming a distributed company happened organically. My co-founder and I were living in different cities when we started the company. He was in film school in LA, and I was working at Google in San Francisco. Our not working together in an office became part of the company's DNA. When we needed to hire part-time employees or contractors, we did it online and found the best person we could, regardless of location. By the time we were hiring full-time teammates, remote was just how we did things. Eventually, we formalized remote work into our company values and made it a part of our mission.

I wrote an entire post on why we work remotely.

How do you keep everyone in the company feeling connected?

Staying connected is a major challenge for remote teams. Like many remote companies, we host retreats to get everyone together in one place. We work together, share meals, and even split an Airbnb house or apartment because we're still small enough for that to be practical.

When we aren't together, we use Slack as our water cooler. Of course, we discuss work stuff on Slack, but we also use it as a place to talk about everything else. The retreats are important, but we try to reinforce online the relationships that we've built in person. Without the retreats, our chat would have a different, work-heavy tone.

Tortuga is unique among remote companies in that you produce a physical product. It's easy to imagine that being able to touch and feel fabric samples, test runs, being in the same place for product photography, etc. would be important. What challenges does that present for your remote team? How do you overcome them?

Making physical products remotely is tough, but we're figuring it out as we go. For starters, one of our teammates, Giulia, lives in China where we manufacture our products. Having her there in person to work with the factories is a huge help. Patrick (our industrial designer) and I visit twice per year to work on products in person. Having everyone together in one room helps us move much faster and iron out any final details on new projects.

Retreats are important, but we try to reinforce online the relationships that we've built in person.

The challenges arise during sampling. In design, everything is online, from sketches to material specs. Then we move into sampling. Without being in the same room or having the factories make multiple copies of everything, we can't all be seeing and touching the same objects. This is the hardest part. Patrick takes the lead but this has meant that I'm less hands on than when we were a two-person company.

We've figured out a process that works at our current size but will have to figure it out all over again as our product team grows. Even when you overcome one hurdle, there's another one right after it.

What is the biggest benefit that working remotely has afforded your company?

Working remotely has allowed us to hire the right people, regardless of location. We've never hired anyone in Los Angeles or the Bay Area, where Jeremy and I are based. For many companies, working remotely is a nice perk, but it is often unrelated to the company's products. For us, it's fundamental to our mission and values.

Our mission is to help people live on their terms. Part of that is being location independent and having the freedom to work remotely. Being a remote company means that we live our mission and can serve as a role model for other companies, founders, and employees. Living our mission also means that we attract teammates whose core values are aligned with ours, not just people who want to work from home in their pajamas.

Do you think anything is lost for your team by working remotely?

Definitely. There are tradeoffs to any choice you make, including whether to have an office. However, we feel we gain more than we lose for what we value as a company and as teammates. For instance, by the time each retreat rolls around, we feel the need for one to get back into sync. Despite my best efforts, we can all feel a bit disconnected with too much time apart.

We've figured out a process that works at our current size but will have to figure it out all over again as our product team grows.

What do you think is the most important thing a distributed team can do to ensure successful collaboration?

Commit to being distributed as a rule, not as an option. Then design all of your communication and project management systems around being remote. If you don't, your remote employees will always be at a disadvantage.

What are some of the benchmarks you use to make sure the team is in a good place, both mentally and operationally?

I have 1:1s via Slack video calls every 1-2 weeks with each member of the team, which is still possible at our size. This helps me to see how people are feeling and to get to the root of problems. Even a video call conveys a lot more information than a text chat.

Operationally, I've been choosing a company-level "theme" each quarter, rather than a numeric goal, so that everyone can set their Quarterly Priorities based on the theme. I find this helpful for setting daily or weekly priorities and to keep our focus on what's important, not just what's urgent.

What sort of culture does Tortuga have? Is it harder to build cohesive culture across geography?

I think that I should ask everyone on the team to answer this then compare our answers. The more similar they are, the better job I'm doing.

Being remote makes a process and results culture important. We've tried to build this culture at Tortuga. "Ass-in-seat time" doesn't matter at a remote company because no one sees you at your desk. Instead we focus on processes (to avoid miscommunication) and results. Results doesn't mean "hit your numbers of you're fired." Results means that we evaluate everything we do, learn from it, and do better next time. When we evaluate opportunities, we focus on high upside while minimizing downside. We want to hit home runs.

Commit to being distributed as a rule, not as an option. Then design all of your communication and project management systems around being remote.

The other important part of our culture is doing epic work and knowing that we either succeed together or fail together. No one person or department is responsible for either outcome. We try to screen for teammates with the right ambition: for the team, not for themselves. If the company does well, they will do well too, as a consequence. The reverse is not always true.

Does Tortuga do anything unique to keep everyone on the same page or bring the team closers?

Retreats are the biggest thing that we do in this regard. The other important pieces are our checkins and recaps. On a remote team, you can easily get siloed into your individual or team work and never talk to your other teammates. We try to over-communicate what we're working on.

Every Friday, we have a team checkin email where everyone says what they accomplished that week, what their priorities are for next week, and where they're stuck.

Every month, we send team-level recaps to share what each team prioritized for the previous month and how it went.

You get together twice each year for retreats. What are the goals you have for that time together as a team? What are some of the things you do to make sure you get the most out of your retreats?

We don't want retreats to be like normal work weeks except we're sitting next to each other. Colocation is worthless if we spend the time with our headphones on staring at our laptops.

The most important part of a retreat is spending time together outside of work tasks. During our three-day retreats, we schedule a fun activity, a volunteering activity, and team dinners. The retreat is three days, but we book an Airbnb for a week so that teammates have more free time to hang out, explore the city, and, yes, even work.

The work parts of the retreat are meant to be inclusive sessions focused on the big picture and the future. Retreats are our time to think big and think ahead. Being together in person and in a new location make thinking this way much easier.

Being remote makes a process and results culture important. "Ass-in-seat time" doesn't matter at a remote company because no one sees you at your desk. Instead we focus on processes and results.

What do you look for in an ideal remote employee? Are there any qualities that make someone more successful at working remotely?

Every job listing is for a "self-starter," but initiative is extra important in a remote company. You have no peer pressure and no one looking over your shoulder. You're working from home. Do you still have the drive to do great work?

We also do an entire interview focused on core value alignment because if someone shares our mission, they will do the work necessary to achieve it.

Describe your personal work environment.

I work mostly from home with time at cafes and coworking spaces to mix it up and prevent my becoming a hermit.

Two years ago, I moved from San Francisco to Oakland for more space. I now have a dedicated home office with a standing desk. Previously, I lived in a studio apartment where my bedroom, living room, and office were all the same room. The extra physical space has given me more mental space and made me more productive.

How do you manage work/life balance when working from your home?

Having a dedicated room and space has helped. At the end of the day, I can close my computer or even the door to my office to signal that I'm "done." If I want to do something online, I can use my phone or iPad. This is the system that I try to stick to. But, I'm still a founder. I let the lines blur and open my computer back up at night when I have an idea I can't get out of my head. I love my work so I don't mind this as long as it doesn't have an adverse effect on the rest of my life.

We don't want retreats to be like normal work weeks except we're sitting next to each other. Colocation is worthless if we spend the time with our headphones on staring at our laptops.

How do you keep distractions to a minimum? How do you personally measure efficiency?

I go overboard with limiting distractions. I have all notifications turned off on my phone except for calls and texts. I'll even put my phone on Do Not Disturb and leave it in another room if necessary. I turn off Slack entirely, not just the notifications, when I'm doing focus work. I don't check email until around lunchtime.

Most importantly, I try to take advantage of my natural rhythms. I do a big block of focus work in the morning, then I eat lunch and go to the gym, then I do the admin work like answering emails in the afternoon when my energy is lower.

What are some of the tools you couldn't live without as a remote company?

Slack, Asana + Instagantt, Dropbox and Google Drive, LastPass, and Astrill VPN.

What do you like to read?

I'm a voracious reader. A few years ago I got an email from Pocket that I was in their top 1% of users. I'm not sure if I should be proud or embarrassed. Outside of Pocket, I'm usually reading one fiction and one non-fiction book at a time. Here are a few of my favorite business books.

What advice would you give to a company heading down the remote working path?

If it's right for you, commit to it and go all in. You can't half-ass being remote. Otherwise, good luck and let us know that you're remote too. I love reading about, talking to, and partnering with other remote companies.

Nearly a decade ago, Balsamiq's founder, Peldi Guilizzoni, set out to build what he called "a little Italian restaurant on the web." A small, cozy company with a homey feel that serves up a great product you want to keep coming back to.

Now, as the team has grown to over two dozen people spread across Europe and North America, the company is figuring out how to keep that corner bistro feel with a larger group. We talked to Leon Barnard, a designer and writer at Balsamiq who has been with the company for four and a half years about what it's like to grow a remote team while keeping true to that home cooked concept.

What does Balsamiq do and what do you do there?

We make a user interface wireframing tool called Balsamiq Mockups. I was a UX designer for almost 10 years prior to joining Balsamiq in 2012. My role is primarily to educate our customers about UX and how to use our product.

How many people are at the company now and how spread out are you?

We are currently 25, but have 4 new people starting later this month. We have a hub in Bologna, Italy (12 people), where most of our development is concentrated. We have a few other people elsewhere in Europe (France, Germany, and The Netherlands; 4 people). And there are 9 of us in the U.S., all working from home, but living in the San Francisco Bay Area or Chicago.

What personally drew you to remote work?

I kind of stumbled into it. I was living in Los Angeles with my in-laws while I looked for work in the San Francisco Bay Area, where my wife and I were planning on moving. A friend-of-a-friend told me about an interesting job with his company in LA. I liked the company and we agreed that I could continue working there, remotely, after I moved, with the plan that I would fly down about once a month. I ended up leaving that job a few months later, but was surprised at how productive I was working at home. I found that it really suited my personality and working style. A while later the Balsamiq opportunity came along and I mostly applied because I loved the product and the company. I didn't decide to work here because it was remote, although it helped that I had a positive experience with it previously.

How does Balsamiq keep the entire team feeling connected?

This is something we're constantly working on. When I started we were around 10 people and it wasn't very hard, because almost everyone was in every meeting. The company was one big team. But even before I started, Balsamiq had organized annual retreats for everyone to spend a week together. That has been crucial. As we've grown our retreats have become less of an opportunity to work together and more of a chance for us just to be together, to have fun and make memories. That bonding has to keep feeding us for the rest of the year. It's harder now, but for a long time we tried as much as possible to live together like a family for that week (by staying in the same house, cooking and cleaning together, etc.).

Your company has a home office in Bologna, Italy. Do you find that having part of the team in the office and others working remotely creates any problems?

Not really, actually. Our founder, Peldi Guilizzoni, worked with an Italian ex-classmate out of his house in Bologna when he made his first hire, but his 2nd, 3rd, and 4th hires were in California, France, and New York, respectively. So remote became the norm pretty quickly.

How do you keep a "two tiered" culture from developing?

Our largest contingent of "Balsimici" is in Bologna, but Peldi has always insisted that we all work as if we were remote. That means that nearly all conversation and decisions take place in chat and on our wiki. Most of our Italian employees only come to the office a few days a week, which makes it even easier to prevent that office culture from forming.

Do you think there's anything the people outside of the office miss out on? Or anything you lose when working remotely that you get when you all work in the same place?

Yes, definitely. I love working from home, but it can be lonely and you feel disconnected at times. I would love to be able to get lunch with my co-workers a few times per week. It's hard to make time to talk about things outside of work. We recently started randomly assigning four people to hang out together, with no agenda, over video chat every Friday. We call it "Friday Funtimes." It helps, but doesn't alleviate the problem completely.

How do you make sure people who don't work in the office don't feel like they're missing out on anything?

Chat (we use Slack) is essential. That's where everything happens. We also have monthly meetings to talk about company stuff (we call it Kaizen) that anyone can join. It's a good place to discuss big picture company things that you might miss out on in your day-to-day work.

I love working from home, but it can be lonely and you feel disconnected at times. I would love to be able to get lunch with my co-workers a few times per week.

What is the biggest benefit that working remotely has afforded Balsamiq?

I'd say work-life balance. I love getting to spend time with my son at this age and being able to eat dinner early together with him and my wife. One of our employees is fulfilling her dream of living in the country and farming. She lives almost two hours outside of San Francisco, there's no way she'd be able to work for us if we had an office there. I think we all get to spend more time with people who are most important to us (our friends and families) and do things that we really enjoy than if we worked in an office. We get to have a life outside of work, in other words. That makes us better employees, because we're happier when we're at work.

What are some of the benchmarks Balsamiq uses to make sure the team is in a good place, both mentally and operationally?

We have always been allergic to metrics, so we don't track very many things, but we have started using tools to gauge how employees are feeling. We've been very pleased with Know Your Company as a way to get a sense of how everyone is doing. And we're experimenting with letting people other than the CEO do quarterly 1-1 meetings (we don't have managers, so, technically, everyone reports to him) because we still want to give everyone time to talk about their challenges and ideas without making that Peldi's full-time job.

What sort of culture does your company have? Is it harder to build cohesive culture across geography?

We really care about each other. I know that sounds trite, but I see examples of it every day. We don't talk about exponential growth, disruption, or valuation; we're just a small company that wants to make a product that helps people make better software. We hire people who are positive and like to make others look good. Everyone knows that our culture is a huge part of our success. It's not our features that set us apart, it's the ease of use of our product and the positive experience that our customers have with us.

We get to have a life outside of work... That makes us better employees, because we're happier when we're at work.

Is there anything unique your company does to connect everyone around common goals and values?

Not having a hierarchy is really important to us, even if it makes some things more challenging. Most policy and company decisions are made by sub-teams of volunteers. Everyone feels like they have a say in the direction and culture of the company. We are always changing and refining our company based on internal feedback and suggestions. Our company handbook has everyone's finger prints on it. Our company is like a garden that we all tend. I don't know how he does it, but, for something that's so important to him, Peldi gives us a lot of control over it. The result of that is that it feels like it belongs to all of us.

Describe your personal work environment.

I work in a converted garage behind my house. It's very basic, but cozy. This is what my desk looks like when it's clean (see below). I have a lot of posters and stickers on the wall that inspire me and remind me of good experiences I've had. There's a futon that I sit on for putting myself into a different thought mode. I'm sitting on it right now. My wife and three-year-old son are often home, so I see them a lot, which is great. Having my own dedicated space is crucial though, so that I can control my interruptions at home.

How do you manage work/life balance when working from your home?

When I'm inside the house, it's hard not to think about non-work things I have to do. That's why the small separation between my house and my garage/office is great. When I'm in my office I'm usually not thinking about non-work stuff. I still struggle with transitions between home and work, though. Having a 5-second commute isn't enough time to re-orient my brain. Sometimes I take a walk around the block before and after work to flip the switch.

How do you keep distractions to a minimum? How do you personally measure efficiency?

I always feel like I'm less productive than I should be. It's easy to forget just how many interruptions and distractions there are in an office, not to mention the time most people spend commuting. I'm pretty sure I get way more done than I ever did in an office, but I still beat myself up for not making better use of my time.

As for distractions, about a year ago we realized as a company that our chat tool was slowing us down. We decided to be more selective about which rooms we read, participate in, and get notified about. That has helped me a lot. I don't need to know what the plugin developer team is talking about, for example. If they need something from me, they'll mention me and I can jump in then. I'm subscribed to less than half of our Slack channels, and most of them I have muted so that I can read them only when I feel like it. My five starred channels are what I rely on for anything important.

What are some of the tools you couldn't live without as a remote company?

Slack, Confluence, Google Hangouts, or Zoom for video conferencing. We've also created our own tool for managing projects.

What do you like to read?

Twitter is my main source of information relevant to my work. I mostly follow accounts that talk about UX, web development, remote working, and documentation. You can see who I follow here. Or you can follow me (@leonbarnard), I mostly just retweet stuff that I find interesting.

What advice would you give to someone thinking about working remotely for the first time?

The company you work for matters even more than it would in an office job. Don't just think about the duties of the job. Disfunction and lack of direction get magnified when people aren't co-located. Here are some revealing questions that can help you learn about a company's culture.

Also, I would much rather work for a company where most or all employees are remote than one where 25% or less are remote. You're swimming upstream if you don't go all-in on remote.

I first met Brian Casel in 2010. At the time, he was a guest writer for Mashable, where I was an editor, and he ran a successful WordPress development consultancy. He did well in that business, but the life of a freelancer takes its toll. As he says on his website, "My income was dependent on me being at my keyboard, working. I was tired of all the busy work. Burned out from living deadline-to-deadline. Stressed from not knowing where the next project will come from."

So in 2015 he decided to start a new company, AudienceOps, a content marketing as a service product that he built with scalability in mind. That also happened to be the same year Casel and his family embarked on a months long road trip around the U.S.

Building AudienceOps as a fully distributed team was natural for Casel -- all of his previous businesses have been remote and, well, he likes working that way. We talked to him to find out more about his approach to building a remote company.

What does AudienceOps do and what do you do there?

Audience Ops offers a fully done-for-you content marketing service. Our team keeps a business' blog running with new, well-researched, high-quality articles published on a weekly basis, then sent to their newsletter and social media channels. We also create and launch lead magnets to help businesses grow and nurture email subscribers.

As the founder, I spend most of my time coaching the team, refining our systems and processes, and I handle most of the sales.

How many people are at the company now and how spread out are you?

Right now, in May 2017, there are 13 people, plus me working on the Audience Ops service. That includes writers, editors, project managers, and assistants.

All of the writers, editors, and project managers are based in the US, across several states. The assistants are based in the Philippines.

In addition, there are 3 software developers who work on our software tools that we've built in-house (and sell to the public). Our developers are based in Eastern Europe.

What led to your decision to build AudienceOps as a remote company?

All of my businesses have been fully remote, for a few reasons:

• The talent pool is enormous. That's a massive advantage over hiring local, in my opinion.
• I like working from home and from coffee shops. :)
• While we do have deadlines and daily/weekly deliverables, I don't like to set strict working hours for my team, nor for myself. The team appreciates that flexibility, especially those who have families and kids.
• Being fully remote keeps costs under control, which is very important when you're fully self-funded / bootstrapped, as we are.

Because your business operates in the service space, it's very high touch. Do you ever get push back from clients who want to meet face-to-face?

Nobody wants to meet in person because all of our clients are remote as well. Most are in the US, but we also have clients in Canada, Europe, Asia, and Australia.

We do have calls with our clients during their onboarding phase, and check-in calls every 2 months or so (varies by client). These calls are hosted and coordinated by our Manager, along with the writer, and they're a standard part of our processes here.

The vast majority of communication happens over email though, and most of our clients prefer this, since most are busy founders/CEOs. A big part of the value we provide is the "hands off" nature of being able to outsource content for their company.

How do you keep everyone on your team feeling connected?

Slack mostly. I encourage (and we have processes) to have the team work together on things and work collaboratively.

If I'm ever traveling to an area where teammates are based, I try and meet up with them. Earlier this year, my family traveled to the Philippines and I got to meet our team who's based there.

I don't like to set strict working hours for my team, nor for myself.

The team appreciates that flexibility, especially those who have families and kids.

What are the biggest challenges you face working remotely and how do you deal with them?

Sometimes there can be a delay in communication and action, which would be less so if we worked in an office together. For example, I do a lot of work in my mornings on the east coast. If I send a request to someone on our team who's in the west coast, they won't see it until at least 3-4 hours from now, etc.

But that's normal and expected for us. We also avoid "rush jobs" at all costs, and keep a very calm and organized production process that accounts for the way we work.

Do you think there's anything you lose when you work remotely?

I worked in a small office environment early in my career, and I do sometimes miss the camaraderie, casual chats mid-day, going out for lunch or drinks together, etc. Also, with a worldwide team, it's more difficult (expensive!) to get everyone together for retreats/meetups.

But at the end of the day, I do think the benefits outweigh those drawbacks.

What do you think is the most important thing a distributed team can do to ensure successful collaboration?

I think it has to be built into your processes. You can't just tell people to work together, because it won't always happen, especially when folks are so used to working solo from home. So our creative process actually requires input and communication from multiple team members.

What are some of the benchmarks you use to make sure the team is in a good place, both mentally and operationally?

We do periodic check-in calls with team members. I also ask our managers to report any issues/ups/downs happening with the team, since they're more connected to the day-to-day work than I am.

What sort of culture are you trying to build at AudienceOps? Is it harder to build cohesive culture across geography?

It is more difficult to build a vibrant culture when you're remote. But I find that a lot of it has to do with the type of people we attract to the team, and the people who end up sticking with us for a long time, vs. don't stick around for long.

I'd say we all share common values: We enjoy creative, challenging work. We value working with a flexible schedule, from anywhere. We're all strong communicators. We all jump at the opportunity to help each other out. No politics here.

What do you look for in an ideal remote employee? Are there any qualities that make someone more successful at working remotely?

• Clear communication above all (no matter the role)
• Self-motivated and self-organized to manage their own daily deliverables and deadlines.
• Constructive thinker and able to suggest ways to improve our operations, make our jobs easier.

I find that a lot of [culture building] has to do with the type of people we attract to the team.

How do you successfully hire great remote employees? What's your process for making sure you find the right people?

When looking for candidates, I use a mix of different job boards, outreach to my network, and referrals from other employees.

We have a process for reviewing applications, saving a short list, inviting to interviews, then onboarding and training.

Some roles require a small test project. But regardless of the role, we find out pretty quickly (within the first month or 2) whether or not someone is a fit. Sometimes they don't work out, often not because of a lack of skill/talent, but because they don't mesh well with our processes and can't reliably deliver on deadlines.

Most of our teammates have been on the team for a year or longer (some over 2 years), and they often give feedback to say this job is easier, steadier, and more reliable for them than others they've had or have. We seek people who fit this style of position, whether it's a part-time or full-time role here.

Describe your personal work environment.

We moved to a new house a year ago, so I had a chance to design my home office. I get nice light in here, which I like. I have an adjustable stand/sit desk, which I love. Macbook Pro + Dell 28" monitor.

1-2 times per week, I'll take the laptop to the coffee shop and work a half-day there, just to mix it up.

How do you manage work/life balance when working from your home?

It can be tough sometimes, especially with 2 young kids at home.

My wife and kids know my normal work schedule, and we have an understanding of when I'm expected to be "at work" or "at home". I try my best to stick to that. Keyword "try." :)

Part of the challenge is the instant switch from work-mode to home-mode. It's tough to shift gears that quickly. So I try and take 20 minutes or so in between, have a beer, take the dog out, to decompress before settling in at the end of the day.

Once I am "home", I keep my cell in a separate room, and I don't read work-related stuff. Watching TV and hanging with the family, reading non-work books, helps me clear my head at night.

Find A+ communicators, and people who've been working remotely and thrive in this sort of environment.

How do you keep distractions to a minimum? How do you personally measure efficiency?

I listen to music most of the day while I'm working. I can't work if there are lyrics though, so I listen to a lot of instrumental playlists and film scores. If the kids are crying in the next room, or I'm sitting next to a chatty group at the coffee shop, I throw on the Bose noise cancelling headphones.

I also plan my week and day before starting work, so I know which tasks are most important. I work on those first, in the morning, when my energy and focus levels are high. I have calls and handle emails in the afternoons.

And I drink Bulletproof Coffee every morning.

What are some of the tools you couldn't live without as a remote company?

Slack. Trello. Google Docs. Gmail. HelpScout. Gusto. GitHub.

What advice would you give to a company heading down the remote working path?

Clear, "above-and-beyond" communication is key. Find A+ communicators, and people who've been working remotely and thrive in this sort of environment.

When Canadian serial entrepreneur Liam Martin met his eventual co-founder, Aussie Rob Rawson, at SXSW, he wasn't planning on jumping back into the startup world. He'd just sold a company and a mutual friend suggested he and Rob meet. Two weeks later, they were working on TimeDoctor.

The team productivity analytics app now helps businesses around the world limit distractions, improve productivity, and gain a competitive edge. We talked to Martin about why he and Rawson decided to build TimeDoctor as a fully distributed company.

What does TimeDoctor do and what do you do there?

We run what we call 'Time Analytics' for remote and in-house teams. We basically sell Google Analytics for your work day so you can figure out not just how long people work, but what they actually do throughout their work day.

How many people are at the company now and how distributed are you?

I believe we're at 82 people and we're in 26 different countries. We have satellite offices in a few countries, but we're primarily remote.

Why did you start working remotely?

Because working in person sucks, the mission statement of the company is to enable people to work whenever they want, wherever they want.

What is it about working in person that sucks?

The biggest reason why people quit a job is politics. There are a lot of longitudinal studies showing that working remotely makes workers happier, healthier, and more engaged in their work.

How do you keep everyone feeling connected?

Skype/Slack, yearly meetups that we have all over the world, a lot of project management and task management systems and video calls every single time we chat virtually.

What are the biggest challenges you face working remotely and how do you overcome them?

Asynchronous communication and lack of processes inside of the business are the two major issues I see with remote teams, making sure you have solid digital processes inside the business and that you have bridge hours in which you can communicate in person are critical, in my opinion.

What is the biggest benefit that working remotely has afforded your company?

Lower costs, higher productivity and the ability to scale much faster than if we were all located in a single location.

Do you think you lose anything by working remotely?

Yes, you lose the personal touch of learning about everyone's day. I think it's a loss I'm willing to take, however, to scale much faster.

Making sure you have solid digital processes inside the business and that you have bridge hours in which you can communicate in person are critical.

What do you think is the most important thing a distributed team can do to ensure successful collaboration?

Documentation of processes and abiding by those processes is, in my opinion, the most important thing you can do.

What are some of the benchmarks you use to make sure the team is in a good place, both mentally and operationally?

We use internal quarterly reports, we also have developed a tool that asks you what your main focus is for the week and whether you achieved it (we call it a rock task) and of course, Time Doctor.

Talk about the company culture you've built at TimeDoctor. What's it like? Is it harder to build cohesive culture across geography?

I actually think we've built a pretty solid culture, building a company where remote is the norm is pretty weird, but we actually hire specifically for that, so it's been pretty fun to see what kind of characters come out of that kind of recruitment process.

What are some unique things your team does to form bonds with each other?

We play DOTA every month, I personally don't play it anymore but a lot of the team still play every month and it's pretty weird.

What do you look for in an ideal remote employee? Are there any qualities that make someone more successful at working remotely?

Three things in order of importance: The ability to take action, reliability, and skill level (i.e., skill isn't important if you can't show up on time and take action remotely).

I think a lot of people... need to [work outside the home] to stay sane.

How do you make sure the people you hire have those traits? When you're communicating only remotely, what sort of things can you to do properly evaluate potential hires?

We have three major tests. Test one is a task that we find important. Lets use a "linker" as an example, we'd have them get us a link without us teaching them anything. Test two, we have them do that for a month and overload them with a lot of work and not enough time to do it in (i.e. we don't show them the shortcuts yet and see if they can innovate on their own) which takes about a month. Test three, we give them all the tools they need to go as fast as possible and see if they can innovate on top of that (about three months).

The whole process takes about four months from beginning to end and we call it the crucible, as we usually burn off the people who can't deal with the speed at which we go.

Describe your personal work environment.

I have a desk I sit at every day with a few monitors, I connect my MacBook Pro when I'm working from my desk, but I often travel, as well. I'll be in four countries over the next two months, as an example.

How do you manage work/life balance when working from your home?

I don't, I actually work outside the home and I think a lot of people also need to do that to stay sane. If that's not an option, creating a focused work space is really important.

How do you keep distractions to a minimum? How do you personally measure productivity?

I actually use Time Doctor for all of that, It's currently taken me 4 minutes and 22 seconds to answer these questions, 4 minutes was spent on Google Apps and 22 seconds on Skype. If I go to a distracting site like Facebook I'll immediately get a popup through Time Doctor asking if I'm still working on writing an email to Josh...

What are some of the tools you couldn't live without as a remote company?

Skype, Slack, TimeDoctor, JIRA, and Basecamp.

What do you like to read? (blogs, books, etc.)

I just finished Rocket Fuel by Gino Wickman which was great. Generally I push audiobooks and podcasts into my head while I'm exercising or traveling and it's about 50% business books, 50% philosophy.

What advice would you give to a company heading down the remote working path?

Hire slowly and build your processes before you scale with remote hiring. You need solid processes in place to scale operations and without them you'll fail.

In 2009, sick of the daily office grind, Sandra Lewis started Worldwide101, a network of virtual assistants based across North America and Europe. The company has grown to a team of dozens, providing VA services (and more) to customers big and small around the world.

How has Worldwide101 managed to keep service quality high while building a distributed team of happy employees? We talked to Lewis to find out.

What does Worldwide101 do and what's your role there?

Worldwide101 supports demanding founders and executives with premium virtual assistants that they can trust to represent them, and their business for the long term.

We differentiate ourselves in three ways:

• First we relentlessly search for top talent. Our premium virtual assistants are selected for their innate sense of service and care, and their years of corporate experience. Both of these key attributes qualify them to become an integral part of our clients’ businesses for the long term.
• Second, we provide customized and personalized support. We get to know our clients’ unique requirements, and only then suggest the most qualified premium VA to support them. Clients get to “meet” and choose their VA before deciding to sign up with us.
• And third, we go over-the-top on support. Our personalized service continues after signup as we work relentlessly to ensure that the partnership is successful for the long term, and offering a lifetime satisfaction guarantee.

Worldwide101 has also recently launched We Are Virtual Assistants, which is a platform to promote excellence in the virtual assistant industry and to provide information, expert advise, tools and resources to succeed remotely, and in a virtual environment.

I am the Founder of both businesses!

How many people are at the company now and how spread out are you?

We have 81 Worldwide101 team members spread across North America, Europe and the UK. We all work remotely and from our home offices.

It seems natural for virtual assistants to be remote -- they're working virtually, after all, and often part-time -- but you also hired remotely for the core full-time team at Worldwide101. What made you decide to opt to build a distributed company instead of getting an office and co-locating everyone in one place?

After working for 20+ years in a corporate environment in the US and the UK, I decided that I wanted a change in pace. And so in 2009, we moved our family to France (my home country) in search for a more balanced lifestyle. It was then that I started thinking about how I could continue to pursue a rewarding career and yet lead a life far away from the stress of a big city, and office politics! So to answer your question, it was my desire for a remote lifestyle, which lead me to build a distributed company, where everyone would have a chance to pursue a rewarding career in their own environment.

I also wanted to give the opportunity to as many talented professionals as possible to join Worldwide101 and to find rewarding work no matter where they are located. One of our key values at Worldwide101 is to promote happiness at work. I believe that the world is quickly moving towards more flexible working arrangements, and that professionals will value more and more the ability to work from home, or from anywhere in the world!

How do you keep your team feeling connected?

We work very closely as a team, and put a huge emphasis on “over-communicating.” Emma, who is our Ops Manager, should really be called our team cheerleader because her only job is to ensure that our growing team has the support they need to succeed. She is the ultimate connector, coordinator, and happiness champion!

Since we don’t “see” each other on a consistent basis every day, we have to constantly be thinking about what to communicate to the team, and ensuring that everyone still feels part of our company.

One of the things that works well and keeps our team connected is their ability to partner to work on client projects or to provide back up for each other when someone is ill or away on vacation. We actually have people who volunteer to be “back ups” because they enjoy “meeting” others on the team!

On a practical note – we have built an intranet with onboarding videos, guides, and a knowledge base. It’s also a place where we post company news, video updates, and team insights. The onboarding is of course accompanied with video Skype meetings to go through the materials “in person,” but the Intranet provides the ability for new team members to learn at their own pace, and to revisit the content, and review procedures whenever they have a question.

We also have a couple of monthly newsletters to keep everyone connected.

And we celebrate birthdays, new babies, and anything worth celebrating!

What are the biggest challenges you face working remotely and how do you overcome them?

Getting everyone on the same page, and hanging out just for the sake of it!

Since we don’t “see” each other on a consistent basis every day, we have to constantly be thinking about what to communicate to the team, and ensuring that everyone still feels part of our company. The expression “out of sight, out of mind” can be quite prevalent in a virtual environment – and so we are doing everything we can to keep everyone in mind all the time!

What is the biggest benefit that being distributed has afforded your company?

We have been able to hire and onboard some very talented professionals from various background, and cultures. When working with a distributed team, our talent pool is significantly expanded, time, energy (and money) is not wasted traveling long distances, infrastructure costs for offices and equipment are reduced to almost nil and employees value the freedom and flexibility. Honestly, for Worldwide101, for our clients, and for our team, it’s only been a win-win-win! Having said that, remote work is not for everyone and so it’s important to know how to hire for success.

Do you think you lose anything by working remotely?

Hanging out just for the sake of it (see my previous answer).

We have a virtual open door policy, we expect people to speak up, and we promote happiness, and long-term partnerships.

What do you think is the most important thing a distributed team can do to ensure successful collaboration?

I believe it’s really important to create an open door policy – or in our case a “virtual” open door policy! Our team knows that they can get in touch with our management team at anytime, and one of our company mottos is to speak up no matter what.

We also try to do video announcements as much as possible, because it’s nice to “see” each other, and it helps us connect on a more meaningful level.

What are some of the benchmarks you use to make sure the team is in a good place, both mentally and operationally?

We are in touch with our team at unscheduled times. So for example, we’ll randomly Skype someone to say hello and for no particular reason.

On a practical level our team’s performance is very much linked to customer satisfaction, so it’s relatively easy to spot when there is something not quite right operationally, and to address it.

What sort of culture does Worldwide101 have? Is it harder to build cohesive culture across geography?

We have a virtual open door policy, we expect people to speak up, and we promote happiness, and long-term partnerships.

As opposed to other virtual assistant companies where VAs get assigned random clients, we give our team a choice of the clients they want to work with based on their preferences (type of work, industries, availability, etc…) We are proud that our team has been with us for years, and so have our clients, and we attribute it to the fact that both parties choose to work together, and commit to making it work!

Do you ever feel any tension between the needs of the VA staff and those on the core team?

No – we all work as a team pretty seamlessly!

Why do you think that is?

I think it comes from the fact that everyone is very clear on his or her role and responsibilities, and everyone understands their place in the organization. We have a marketing and sales team promoting our services, and speaking with customers, and we have operations supporting our team, and then our team of VAs supporting our clients! Our company is pretty lean.

What do you look for in an ideal remote employee? Are there any qualities that make someone more successful at working remotely?

We look for individuals who have made a conscious decision to work remotely. These days, with the rise of flexible working, many people apply for our positions without having necessarily thought it through, and because it sounds like novel idea to work from home. We look for applicants who desire this lifestyle, who value the flexibility that it provides, and who will work hard to retain that privilege.

We also look for professionals who have excellent communication skills both verbal and written. We do a lot of emails, so clarity of communication is key to succeed in a virtual environment.

Describe your personal work environment.

For the past year I have spent most of my time in a rural part of South West England. I have a home office looking out to sheep and lambs, and I really appreciate the bounty of nature, and the peaceful feeling it brings me.

How do you manage work/life balance when working from your home?

It’s hard to disconnect when you work from home. The only thing I found that works is to walk my dogs, and I am very grateful that they beg to be taken out or I might never take a break!

Clarity of communication is key to succeed in a virtual environment.

How do you keep distractions to a minimum? How do you personally measure efficiency?

I work in blocks of time. That is, I find that it’s more efficient to schedule two afternoons a week with meetings back to back instead of having days of meetings and personal work. Somehow the blocks of time to do different tasks have been more conducive to my productivity.

What are some of the tools you couldn't live without as a remote company?

Skype, Slack, and Google Apps. There are a few more but these are really essential.

What do you like to read?

I recently finished reading Raising the Bar by Gary Erickson. It’s a fantastic read about integrity in life and business, and a very inspiring story about living life with passion and creating a good environment for employees to succeed and be happy.

What advice would you give to a company heading down the remote working path?

Lay a solid foundation before thinking of growing too fast. When your entire team is remote it’s easy to plow along without noticing there is an issue or someone is completely not onboard! Take your time, listen to people, reach out often, and create processes, which will allow for growth.

When Dave Nevogt and Jared Brown started employee time tracking app Hubstaff in 2012, they were utilizing freelance talent spread all over the world. As the company grew, it was only natural to hire and manage their team in the same fully distributed way.

The Hubstaff platform has grown in the years since to include payroll, timesheets, and scheduling features, as well as the freelance talent marketplace, Hubstaff Talent. Hubstaff, which is now used by over 8,000 teams worldwide, describes its platform as a way to help "businesses with distributed teams operate more smoothly."

Here is cofounder Dave Nevogt on how Hubstaff is eating its own dogfood and building its remote team.

What does Hubstaff do and what do you do there?

We help companies scale their use of freelancers. We do this via time tracking software, a freelance marketplace and project management software. I set the vision, strategy, run marketing and support.

How many people are at the company now and how spread out are you?

33 people and we are all over the world. I think ~10 in the US, ~10 in Europe and ~10 in Asia.

Why did you decide to build Hubstaff as a fully remote company?

I've been running companies since 2003 and I've only run one in that time that hasn't been remote (and they were the 2 most unhappy years of my life). So it was a happiness thing for me and feels more natural. My personality needs it.

How do you keep everyone feeling connected?

Slack does this for the most part. We also have a culture development team and try to do things to show we care. We talk about regular things on Slack and are planning our first retreat.

Given the nature of your business, you obviously work with both full-time employees and remote freelancers. That's an increasingly more common occurrence for startups. How do you keep freelancers looped into the company values and vision? Do you think it's easier when the entire full-time team also works remotely than if you were all in an office together somewhere?

This is something I have been working on. First you've got to actually develop the vision, and most of the time that happens after you've hired a lot of people (as in our case). But I do think think it's important that everyone understands what we are building and why. So we'v been trying to work on everyone contributing ideas to the product development team, everyone writing blog posts and everyone working on customer support - if you know your customers and target audience then you'll have a lot better idea of what the vision really means.

The main advantages are that you can find better people for less money because of sheer quantity.

What are the biggest challenges you face working remotely and how do you overcome them?

Priorities are the biggest challenge with remote work. It's a little easier for problems to continue and never be resolved because you don't have that opportunity to really get together in the same room and work on a problem until it's solved. So there needs to be a good manager in place to really work on priorities and look at bottlenecks from a high level and work on widening those.

What is the biggest benefit that working remotely has afforded HubStaff?

Talent and cost. The main advantages are that you can find better people for less money because of sheer quantity. There may not be a great, available graphic designer in Indianapolis for $45,000 annually. But maybe in Bulgaria there is a world class talent, or maybe they exist in rural Kansas where they need to live because they are taking care of their mother at home.

You also get cost savings based on lower overhead and team members not having to commute.

Do you think you lose anything by working remotely?

You lose the feeling of tight friendships in the workplace, I think, which can lead to people not feeling as committed to the mission of the company.

What do you think is the most important thing a distributed team can do to ensure successful collaboration?

One thing is staying small. In our experience the CEO, for example, cannot be connected effectively to 30 people remotely. So we've made the decision to keep the team smaller and keep the vertical management structure so we can continue to collaborate with each person and know them individually.

What are some of the benchmarks you use to make sure the team is in a good place, both mentally and operationally?

I check in with people personally and ask if they are happy and if there are changes that need to be made. For operations, we have a whole document that we update on a monthly basis that tells us where the business is. We are also a transparent company, so all the financials can be found here.

It's hard to really get to know someone closely from thousands of miles away despite working together for over 8 hours a day.

In talking to dozens of remote teams, a commitment to transparency is a theme that has come up time and time again. But as you said, Hubstaff goes a step further by sharing a lot of its core metrics not just internally, but publicly. Why did you decide to do that?

We decided to do this a long time ago and it was something we considered closely but in the end we felt that the positives outweighed the negatives. The main reason for doing this was that it felt like being transparent would help give our company an identity and it's worked really well. It helps us tell our story better.

Describe Hubstaff's company culture. Is it harder to build cohesive culture across geography?

It is harder to build a culture I think. It's hard to really get to know someone closely from thousands of miles away despite working together for over 8 hours a day. All of that being said I do think that our culture is good, and it's driven by using data vs. opinions and planning products and marketing before we start building. These are really the phases where our team works well together because it's not about one person making a decision, it's more about dealing with facts and working through those and moving forward.

What are some of the unique things you do to keep employees motivated, connected, or on the same page?

I don't really allow email for communication because it's a one on one environment and things get lost. So we really require that communication takes place in our project management tool (just released into beta). This way everyone can see what everyone else is doing, and it contributes to transparency as you mentioned earlier.

What do you look for in an ideal remote employee? Are there any qualities that make someone more successful at working remotely?

This is one of the most important things that I do, I believe. I am the one who finds most of our team members and something that I take pride in doing. When looking for a remote employee I look for honesty, accountability and experience as the top 3 things. 2 of the 3 are personality based. I am really looking for someone thats going to be a good fit for our team and THEN that they have the skills.

Describe your personal work environment.

Posture has become important to me because I spend so much time in front of the computer. So I have a monitor at eye level. Most of the time I am sitting in an office chair with the monitor into a built-in cabinet. Jared and I joke that we are "hunkering down in our caves," but really we don't want to change this way of working. We don't see the advantages or going to the coffee shop a whole lot, or going to a lot of events. Just being heads down and cranking things out works well for us. We are usually listening to music and just getting stuff done with our teams.

On an individual level, do you manage work/life balance when working from your home?

It's gotten a little harder now that I have kids because there are school pick up times, more noise, etc... I try to spend a lot of time with my kids and for the most part they leave me alone when I am working. Working from home was never a problem for me at all in terms of focus, but there is more and more going on and I am finding smaller chunks of time to truly focus. I try to get up early in the morning when things are very quiet and I am morning person by nature. I usually don't work at night other than trying to clear some emails.

How do you keep distractions to a minimum? How do you personally measure efficiency?

Keeping distractions to a minimum usually involves locking the door and cranking up the music (usually jazz if trying to focus). Personal productivity = if my team is filled with work and I am knocking priority items off my to do list (which is all tracked via our PM tool).

What are some of the tools you couldn't live without as a remote company?

PM software, our own time tracking for management and payments, Slack, Jing, Dropbox, and Google Docs.

What do you like to read?

I used to read a ton. Now it's mostly golf books, though, because I feel that we know what we need to do in order to grow, so I try to focus on other areas.

What advice would you give to a company heading down the remote working path?

I'd say start small – start with 1-2 days a week and see how it works. Or start with a few employees and see what happens. If you don’t find negatives with that setup then expand it.

CoLab is a worker-owned web agency that focuses on providing digital design, development, and strategy services to nonprofit organizations and companies that have a social mission. Though the company operates its own co-working space in upstate New York, they have cooperative owners and freelance collaborators spread out across the world.

Ralph Cutler, one of the founding worker-owners, discusses how CoLab manages its globally distributed team and why remote work was an obvious choice for the group.

What does CoLab do and what do you do there?

We provide web services and strategy to organizations doing work that matters.
As worker-owner I do many things, but mostly design.

How many people are at the company now and how spread out are you?

We have 8 worker-owners with about 20 regular collaborators. We are spread around the world:

Upstate NY, US
Brooklyn, NY, US
Austin, TX, US
Bay Area, CA, US
New South Wales, Australia
Montreal, Canada
Punjab, India
Maharashtra, India
Caerphilly, UK
Taichung, Taiwan
Izola, Slovenia
Jakarta, Indonesia

Why did you decide to build a remote company?

We saw it as a strength. We think globally, like the saying goes, and it was a natural progression coming from freelance work that was often remote. Think about the fact that as a design firm, we are never asleep -- someone is always awake.

How do you keep everyone feeling connected?

Everyone comes to CoLab through a personal connection, so we trust good people to bring in good people. We use chat tools, we schedule check-ins and less formal meetups. We visit each other in person to get to know each other when we can. We experiment and work to build a culture of compassionate, genuine loving people where they are really valued for who they are and not just how badass they code.

CoLab is also a worker owned cooperative. Does having a team spread out across multiple countries complicate things for you with regards to this ownership structure?

We optimize as much for budget and quality as we do for collaboration and interpersonal growth. Unlike many design firms, which fire and hire based on work alone, we hire and allow for personal transformation. This aspect of our value system aligns with many of the clients we work with; or they aspire to work in this way and draw inspiration from us for caring about people as much as profit.

International communication does complicate our work from a technical standpoint in terms of institutional and project-based memory. That said, it does not complicate things in the way we conduct ourselves, make decisions, or run operations.

Slight aside: What made you decide to form as a cooperative? What are the advantages to that structure?

We like empowerment, we like freedom, we like democracy. We think hyper-competative economies based on exploitation and survival of the fittest are archaic and doomed to fail, or just destroy the planet. We felt is was the the best way to walk the walk and stay true to our intentions and hopes for the world, while providing a livelihood for ourselves.

Take a moment in silence and stillness together to experience your co-worker's mood. Become masters of empathy, know each others strengths and always be looking to improve communication skills and carve out time to travel and see each other face-to-face.

What are the biggest challenges you face working remotely and how do you overcome them?

For me not having someone around to just ask a small or stupid question, to get out of my own head with some sketch or idea and find a groove to go on impromptu. Sometimes that works, but it’s easier with someone next to you in a space.

**What is the biggest benefit that working remotely has afforded your company?

Someone is always awake and ready to work. It helps us provide great value to the partners and clients we serve.

Do you think you lose anything by working remotely?

It would be nice to shake hands, dance together, hug, or buy someone a coffee more often. Those things happen, it’s just more spread out.

You also operate a coworking space in Ithaca, NY. Is it important that you have that physical space for people to work from or do you think it doesn't have much impact on how CoLab operates?

Yeah, we think it’s important.

We think it’s great to have smaller hubs where a few CoLabrs are together. It is a place for others to visit, a place to foster culture, and bring energy to the team. It also creates greater opportunity for CoLab to contribute to that local community.

What do you think is the most important thing a distributed team can do to ensure successful collaboration?

Start every meeting with a check in about what is going on for each person. Communicate with one another face to face in real-time over Skype or Google Hangouts or Zoom. Take a moment in silence and stillness together to experience your co-worker's mood. Become masters of empathy, know each others strengths and always be looking to improve communication skills and carve out time to travel and see each other face-to-face.

What are some of the benchmarks you use to make sure the team is in a good place, both mentally and operationally?

Responsiveness and productivity are good indicators. When a CoLabr goes quiet it's usually a sign that they need some additional support. We also do explicit checkins, giving everyone a chance to report on how they're doing/feeling about their work and in general. We also have peer reviews and project retros.

What sort of culture does your company have? Is it harder to build cohesive culture across geography?

Everyone comes to CoLab through a personal connection and a connection to collaboration and interpersonal transformation. Good people are magnets for other good people. That part is a bit magical. People find us, they can sense in part through our work, through our model, and instinctively that something different is happening here.

What do you look for in an ideal remote employee? Are there any qualities that make someone more successful at working remotely?

It is a question we ask and when we look at a candidate for a job it is a consideration just how comfortable we think they will be in a distributed environment. However we look for the same things in a remote person as we do for someone who would be at our Ithaca coworking space. We want people who are authentic, seeking community in the workplace, have a strong desire to make the world a brighter place, and want to learn and grow (themselves, in their craft, in collaborating with others).

Good people are magnets for other good people. That part is a bit magical.

Describe your personal work environment.

I work in a dedicated home office / guest room. It’s a new set up because I just moved to Austin, TX. It’s pretty minimal. CoLab affords its owners an ergonomics stipend, so I have a nice chair, a simple white desk, pro color monitor, Bluetooth keyboard and mouse, and my Macbook Pro stacked on some books. There is a convertible couch/bed in the room and a nice-sized window. The walls are pink and orange. I kid you not, porange. I am thinking about what to put up on the walls ,but for now it’s just a picture my son drew with him, his brother, Mom, Dad, and Laya (CoLab co-cowner Ethan’s one year old daughter).

How do you manage work/life balance when working from your home?

I have two kids under five and we just moved to a new state, so it’s all just kind of a glorious shit show right now, but being home allows for great flexibility when family life needs attention.

How do you keep distractions to a minimum? How do you personally measure efficiency?

Remote workers need to be very self-motivated, disciplined, and organized.

It’s kind of simple for me, I have between five to seven hours of “office” time on any given work day. If I haven't been able to log close to that in work because I took too many trips to the fridge, I need to focus better or go for a walk to reset.

CoLab owners also have team all hands meetings each week. So whatever I say I’m going to do this week, I’ll be reviewing next week in front of other team members.

What are some of the tools you couldn't live without as a remote company?

Oh man, over the years we’ve had them all including some custom built ones. We can’t live with out JIRA or HipChat right now, but that’s not to say we don’t dream of a better solution. By the time this goes live, we’ll probably be off HipChat and onto Slack.

What do you like to read?

Stories to my kids!

Lately I’ve been reading about typography and CSS on misc blogs. I was geeking out on 8 point grid methods the other day. I like magazines. Medium has some good stuff on politics and music, though I grow tired of those “How to hack yourself, the market, your job... to be rich or more awesome or build something 'useful' in 30 minutes"-type posts.

Austin has some great bookstores; I’m looking forward to going to one and getting an actual book to read soon.

What advice would you give to a company heading down the remote working path?

Find honest, trusting and open people to do it with.

When TeamGantt was bootstrapping their first product, a visual project management tool, they didn't have the money to rent an office space. So the two founders worked from their homes in Maryland.

Now, even though the company has grown to more than half a dozen people, they still don't have an office and the founders still work from their homes. In fact, most of their employees live thousands of miles away from them. The decision to hire remotely is one that they directly attribute to their fast growth (they now have thousands of customers including multiple Fortune 500 companies) because, they say, it has allowed them to be more productive.

Here is co-founder Nathan Gilmore on why he thinks that is, and how he keeps his growing business humming along smoothly with employees across the U.S. and on opposite sides of the globe.

What does TeamGantt do and what do you do there?

TeamGantt is a simple project management software that allows people to visually plan out their projects and execute them in a beautiful timeline view. I’m a co-founder and product designer.

How many people are at the company now and how spread out are you?

We are a team of nine people now, with people in Maryland, New Hampshire, Oregon, Rhode Island, Georgia, and the Philippines.

Why did you start working remotely?

It was just myself and John [Correlli] for the first few years of the company. We would work from our homes Monday-Thursday and then get together at his house on Fridays to go over any tweaks for upcoming releases. We always joked about how we wouldn’t get anything done if we always worked in the same office since we end up talking a lot on Fridays.

So it was natural for us as we built out the team that we decided to keep things remote as we really enjoy the ability to get long stretches of focus in without interruptions. We’ve been way more productive this way. Another big benefit is attracting talent. It broadens the talent pool big time. We get hundreds of applicants every time we post a job opening.

How do you keep everyone feeling connected?

We use tools like Google Hangouts for meetings which is fantastic. It really feels like you are connecting with people. Some people we would hire and just get to know over Google Hangouts. Then we’d meet in person and we felt like we already knew them. We also do something similar to a daily standup each day and manage it through TeamGantt. This way, everyone knows what we are all working on each day.

We also do a few meetups or company retreats each year. Earlier this year we did a company wide retreat to the Poconos in Pennsylvania. Everyone brought their families, too. It was a great time where we all got to spend time together and get to know each other and our families.

You've written that remote work helps facilitate focus and boost productivity for your team. Can you explain how and why?

Yes, it’s simple. We don’t have the daily interruptions that you get in an office. We don’t have people stopping by our desks to chat or interrupt us while working. Interruptions during the day are a huge productivity cost because of the time to stop and restart a task. We can really stay in the zone for hours at a time.

[Remote work] broadens the talent pool big time. We get hundreds of applicants every time we post a job opening.

When you started, remote working was a necessity. Now that you could presumably afford office space, are you ever tempted to get one? Do you think you're missing anything by not having a space for the team to physically congregate?

We really aren’t tempted at this point at all. Especially now that over 1/2 of the team isn’t in Maryland, it wouldn’t make sense to have an office for just a few of us. Plus, we all enjoy working at home. A lot of us have small kids and we get to see them more often.

What do you think is the most important thing a distributed team can do to ensure successful collaboration?

Communication is key. It’s important to figure out what tools work best for you. We use a mix of TeamGantt, Slack, and Google Hangouts. The in person meetups are also super important. It really helps to connect everyone and remind each other that we are in this together.

We also just adopted John Doerr’s OKR system for helping to align Objectives throughout the company. This way everyone can know what the company is trying to achieve and how each person’s individual objectives alight with the company objectives for the quarter. It’s something we actually just put in place recently! Maybe we can provide an update on how this works for a distributed team down the road.

[Editor's note: we'll do a follow up interview with TeamGantt in the future to see how this system has worked.]

What are some of the benchmarks you use to make sure the team is in a good place, both mentally and operationally?

I try to talk to people individually about this to get feedback on how they feel about their job, the company, and how connected they feel to the company. We’ve been making adjustments based on feedback.

What sort of culture does TeamGantt have? Is it harder to build cohesive culture across geography?

A big part of our culture is work/life balance. We ask for 40 smart, hustling, working hours. Then after that, we encourage everyone to leave and spend time with their families. Everyone is pretty good about sticking to this. A lot of us all have stuff in common too, whether its kids, a love for the outdoors, different hobbies, etc. We also defined our mission statement and core values on our last retreat, which helps to set the tone of our culture.

We don’t have people stopping by our desks to chat or interrupt us while working. Interruptions during the day are a huge productivity cost.

Really though, the culture is defined by the people in the company. We try to hire people that would be a good culture fit, and so far everyone fits in perfect. We all enjoy hanging out together even if it’s not work related.

What do you look for in an ideal remote employee? Are there any qualities that make someone more successful at working remotely?

They need to be self motivated and disciplined.

Describe your personal work environment.

Since I work from home with three small kids, ages one, three, and five, we had to come up with a plan as a family of how to best manage this. The plan is actually very simple. I have a dedicated office space with doors and my wife and kids know to give me my space from 8:00 am to 5:00 pm each work day. However, at 5:01, if I’m still in there, a kid may come in to remind me that it’s time to stop working for the day. I then shut things off and leave the office and my computer for the night. Then it’s family time.

These boundaries have played a huge role in being able to successfully work from home. I’m a big believer in separation of work time and family time.

As far as my actual office space, I have a motorized Ikea standing desk, lots of natural light, plants, and lots of white. That’s the great part of working from home. You can design your office exactly how you want it.

How do you keep distractions to a minimum? How do you personally measure efficiency?

I’ve always been very disciplined with this. Structure is everything with working from home. To me, surfing the web, doing lawn work, or house chores during my 8-5 working hours is cheating. So, I force all of that to be either on my lunch break or after 5:00 pm. know that if I give it my all from 8:00 am to 5:00 pm, I can comfortably relax at night knowing that I worked a solid day. Night time is for family and relaxing so that I’m ready to go the next day.

I always have one really big thing that I want to achieve each day. Typically it’s a new feature design that I’m working on. Before working on email or anything else, I start on that one feature that needs to be designed. I’ll work on that for a few hours first thing each day while my mind is fresh. Once I accomplish that, I either continue to iterate on it or tackle more tasks for the rest of the day.

What are some of the tools you couldn't live without as a remote company?

Google Hangouts and TeamGantt.

What do you like to read?

I’m going through Work Rules! by Google's Laszlo Block right now. It’s a great leadership and business book about how Google had so much success. It’s helpful for us as we start to shift from a super small team into a growing team.

I also love to listen to podcasts about startups and learn from the experiences of others growing similar businesses.

What advice would you give to a company heading down the remote working path?

Make sure that your team feels connected and make adjustments if they don’t feel the connection. Listen to what would make them feel more connected. Is it using a different tool to collaborate, doing in person retreats, or have company goals to try and achieve together, etc.?

As flexible work arrangements become more common place and more people begin to telecommute, many companies with traditional offices will need to figure out how to communicate with team members in multiple locations. Companies have long dealt with the issues of multiple office locations, but having numerous employees and contractors working from home, in different timezones, and with different schedules presents a new set of challenges.

Smartly (part of Pedago) has had to figure out both -- connecting two nearby office locations along with several remote employees and contractors spread out across the country. Below is an interview with two of Smartly's cofounders -- Alexie Harper and Ori Ratner -- on how they're managing to make it all work.

What does Smartly do and what's your role there?

Harper: Smartly is a new educational technology company that's out to change how we all learn. We help companies and individuals succeed by making learning dramatically faster and more effective, with highly interactive lessons conceived for the smartphone era.

We offer a highly selective MBA degree with courses in Finance, Marketing, Management, and Entrepreneurship that is completely free for admitted students. We partner with great companies that recruit Smartly students looking for new career opportunities. These companies pay us for the privilege, which helps keep the MBA free to every accepted student.

Ratner: As CTO, my team and I are responsible for constructing and maintaining the Smartly web and mobile apps, including our internal content authoring platform.

Harper: As the CPO of Pedago, I collaborate with Ori on designing the product experience and lead the content creation team in developing Smartly content.

How many people are at the company now and how spread out are you?

Harper: We have 21 employees spread across seven states. Our main office is in Washington, D.C., but we have a small office in Harrisonburg, VA as well. Six of our employees work remotely from Los Angeles, San Francisco, Boulder, College Station, New York City, and Indiana. We also have employed contractors spread out around the world for various projects.

Why did you decide to start hiring outside of the company's home area?

Harper: As soon as we expanded beyond the founding stage, we set up our two offices in DC and Harrisonburg, VA. We had previously worked at a company with offices in both locations (Rosetta Stone). Even though we were based in the DC area, we knew a great group of people in the Harrisonburg area that we were eager to work with. Because we set up our company structure to work with multiple locations, it wasn’t a stretch to hire contractors around the country to work with us in the early days, and many of those contractors went on to become full-time employees.

You have both an office and a group of people working around the country. There are some remote work advocates who believe that it's an either/or proposition -- you can't have both an office and a remote team or you end up with divergent rules and cultures. How have you kept everyone in sync?

Ratner: A few things have worked out in our favor. First, we actually started out not with one office, but two. So instead of a “home base” and “remote worker” dynamic, it was more like two satellite offices. Second, the founding team knew each other, so there was trust and shared culture despite the distance. Finally, from the very beginning we were very deliberate about setting up tools to support remote work and encouraged their use. In practice, this means favoring chat rooms and video hangouts for meetings, pair programming, etc.

What are the biggest challenges you face with remote work and how do you overcome them?

Ratner: At the basic human level, we want to keep the team feeling connected to one another. We have a lively chat room culture, like many tech companies, but we also have found that other modalities, including video chat and screensharing, are equally important.

There’s still no replacement for getting together and brainstorming in the same physical space.

From a management perspective, it’s important to be able to track time and deliverables from employees in disparate time zones and with differing work schedules. Tools like Toggl can be very helpful in this regard.

On the flip side, what are some of the benefits that you've noticed from having part of your team work remotely?

Harper: Retention is much easier when you support remote work. Since founding the company, several employees have had kids, moved across the country, and even lived abroad for a period of time. In all of these cases, having the mechanisms in place to support productive work outside of the office has allowed us to retain good people. And of course, hiring is easier when you don’t need to restrict your search to local or open-to-relocation applicants.

Do you think anything is lost when working remotely? Is there ever a time you wish everyone was just in the office with you?

Ratner: Despite all of the technology available today, there’s still no replacement for getting together and brainstorming in the same physical space.

What do you think is the most important thing a distributed team can do to ensure successful collaboration?

Harper: In our case, we found it was making time for face-to-face conversations over video chat. There’s an empathy gap that can develop if you don’t take the time to have a conversation and look each other in the eye.

What are some of the benchmarks you use to make sure the team is in a good place, both mentally and operationally?

Harper: Operationally, tools like Toggl and Trello help us track time on task and project progress. Our daily standup meeting over video chat is helpful to collect thoughts and concerns from the team. The most effective strategy is also the most obvious: communicate with one another regularly, building in enough schedule flexibility for ad-hoc conversations.

What sort of culture does your company have? Is it harder to build cohesive culture with some team members living on opposite coasts?

Ratner: The most important ingredient in a company’s culture is who you hire. We’ve had good luck hiring people that are self-starters who appreciate both the increased freedom and responsibility that remote work entails. Unsurprisingly, people like this enjoy working with other driven, self-motivated people, remote or otherwise. The rest is details.

Have you done anything fun in the past to bring remote and office team members together? Like what?

Harper: We’ve had a few all-company events to bridge the gap between remote employees. Holiday and launch parties have been opportunities to bring everyone together, including family. Before we expanded to additional locations, we would often have sprint planning at a 4H summer camp (!) that was located roughly halfway between our two initial offices.

You also work with a number of contract writers who are spread out around the country. How do you fit them into the mix? Is it easier to deal with contractors because you already have the remote framework in place or does it make it more difficult to separate full-time and contract employees since you don't have the natural barrier of physical location?

Harper: We work with a variety of contractors in different capacities, but typically they are looking for more schedule flexibility than our full time employees.

What do you look for in an ideal remote employee? Are there any qualities that make someone more successful at working remotely?

Harper: We look for people who are self-motivated and passionate about what they do.

How do you keep distractions to a minimum? How do you measure efficiency?

Harper: On the content team, we set ambitious but fair goals for ourselves. We create target dates for each lesson based on past performance and use tools like Trello, Toggl, and Microsoft Project to keep on track.

Ratner: On the dev side, agile processes like Scrum give us a set of metrics to track progress within the Sprint and the mid-range plan. The daily standup meeting allows us to observe and readjust if things get a little off-track.

What are some of the tools you couldn't live without as a remote company?

Ratner: HipChat, Trello, Toggl, Google Hangouts, Screenhero, Drive, Dropbox, Git, and Google Docs.

What do you like to read?

Harper: A few of our favorite authors, books, blog, and articles:

• Mindstorms by Seymour Papert
• Bret Victor’s interactive explanations
• Steven Pinker
• On Writing by Stephen King

What advice would you give to a company heading down the remote working path?

Ratner: Minimize email. It’s the lazy way out, and in our experience leads to fatigue in a way that chatrooms, video chat, task boards, and wikis don’t. Think hard about what type of information belongs in each tool, and establish expectations up front. Make a conscious effort to model the behavior your want to see in your employees, from documenting decisions on a wiki to simply announcing when you’re stepping away from your keyboard in chat.

Harper: When you’re remote, even the small gestures can make you feel more connected to your coworkers.

Luke Ryan has been working remotely for the past five or so years. But it wasn't until he joined software development firm Mokriya that he got a chance to be part of a team in which everyone is remote.

Below we talked to Ryan about remote working, how Mokriya builds and organizes its growing team, and his experiences working for different types of distributed companies.

What does Mokriya and what do you do there?

Big companies hire Mokriya to build amazing software for small devices. Our strategic development approach for mobile, IoT, connected devices and more is being used by millions of people around the world. I head up our marketing team.

How many people are at the company now and how spread out are you?

We are now 45+, scattered all over the world. We have team members on almost every continent!

You've been working remotely for a while, what made you decide to pursue this type of work environment?

I’ve always had an affinity for travel. I have family in Australia but am connected to communities in Sweden and the US also. So working remotely is ideal for being able to spread my time across these different locations.

Why did Mokriya decide to build a distributed team?

First and foremost, access to the best talent. We did not want to be limited to the Bay Area, where Sunil, our CEO, first set up the company.

How does the company keep everyone feeling connected?

We have a collection of tools and habits that keep us well connected.

Slack is the hub for communication. We use Zoom for syncs and other team-based or all hands meetings. Having a virtual daily standup is also a nice way to keep everyone connected and on track.

What are the biggest challenges you face working remotely and how do you overcome them?

I think personally, its a challenge to ensure you don’t feel lonely and you also obviously need to self-motivate to an extent. So it's naturally suited to people who are comfortable working alone and in an autonomous fashion. But by utilizing the communication tools and building a culture of transparency and support, these challenges can be overcome. Working from a co-working space or cafes can also be a good way to combat loneliness.

What is the biggest benefit that working remotely has afforded your company?

Apart from the talent access, it simply allows everyone to be more authentic and happier. By working from wherever in the world you are most happy and productive, well, that’s an amazing benefit as well as a competitive advantage.

Compared to the previous remote startups you've worked with, what does Mokriya do differently?

I’ve worked in teams where there were remote elements, but they were not “remote first” companies. Mokriya is remote-first 100%. This places everyone on the same wavelength and its prohibits any feelings of uncertainty in your mind, allowing you to just focus on what you do best.

[Remote work] allows everyone to be more authentic and happier.

Running this blog, I come across a lot of companies that are 100% remote and some that have a split culture with an office or two and then a big chunk of remote workers. As someone who has worked in both types of environments, what are the big differences? What are some things you feel like you can do at Mokriya, that were missing from previous places where you were remote but others where in an office somewhere?

The biggest difference (and most important) is a universal wavelength that the entire company is operating on. For example when a company is remote-first, remote communication and other value are engrained in the culture. The danger I have witnessed in the alternative split culture is that there can be opposing forces chipping away at the morale and culture of the company. Of course it doesn't have to be this way, but is a risk when you have a bunch of people in the office on one wavelength, chatting at the water cooler, holding spontaneous whiteboard meetings, etc., and then the remote group. The remote group may be on an entirely different wavelength, in some cases treated differently and communicated with differently. This is less than ideal.

As to Mokriya, by having a remote-first culture I feel 100% confident in my trust granted from colleagues, as well as the trust I grant to them. This alone, is a huge and beneficial aspect to having the remote-first culture.

What do you think is the most important thing a distributed team can do to ensure successful collaboration?

Commit to remote-first. Commit to certain processes and systems, have a solid onboarding for new hires. Embrace a set of values that foster transparent and supportive employees.

What are some of the benchmarks in use at Mokriya to make sure the team is in a good place, both mentally and operationally?

We use regular syncs between teammates and daily standups for teams. Generally just having a strong culture of open and transparent communication, a lot of which passes through Slack.

What sort of culture does your company have? Is it harder to build cohesive culture across geography?

Its best summed up by our values but a real passion for our craft and transparency are big features of that. I don’t think it's harder. If everyone lives the values, it doesn’t matter where we are geographically.

What do you look for in an ideal remote employee? Are there any qualities that make someone more successful at working remotely?

Great written communication. An ability to work autonomously. Someone that grants trust and brings their authentic self to work.

Describe your personal work environment.

I always sit at a co-working space, no matter what city I’m in. And then, set up my Macbook Air with a thunderbolt display and focus primarily on getting my posture and eye level height correct.

How do you manage work/life balance when working from your home?

During the days I do work from home, I relentlessly schedule my work hours with specific tasks. Then I hold myself accountable to that plan.

How do you keep distractions to a minimum? How do you personally measure efficiency?

Good music, with earphones in, helps me avoid distractions. Taking meetings only in afternoons helps keep mornings free for most important tasks. I know I’m being efficient if my to-do list is getting completed -- if its not, then I know I’ve fallen victim to too many distractions.

What are some of the tools you couldn't live without as a remote company?

Slack, Asana, Google Apps, Dropbox, Zoom, GitHub.

What do you like to read?

I keep Twitter and feedly optimized for marketing, mobile, IoT, and company culture news from a bunch of great influencers. Books tend to focus on mindfulness lately. The Untethered Soul was super impactful.

What advice would you give to a company heading down the remote working path?

Go all in! Read and seek advice from those already blazing the trail. Set up and then live your values.

When Marianna Boguslavsky launched her digital agency in Dubai, she suddendly found herself supporting clients in two places -- in Cape Town where she'd previously operated, and now also in the UAE. It was natural, then for her to hire team members in both places and allow them to work remotely.

That was also a good fit for Boguslavsky, who lives a "digital nomad" lifestyle, living and working on the road from across the globe. Last year she spent time in the UAE, South Africa, New Zealand, Indonesia, and Singapore.

Pajamas talked to Boguslavsky about what it's like to build and run a company from the road.

What does your company do and what do you do there?

I run a niche digital strategy agency (http://www.boguslavskyandco.com), working primarily with SMEs and startups, and focus on helping them grow their brand presence and achieve their business goals through digital marketing.

How many people are on your team and how spread out are you?

There are five of us -- I'm the MD and digital strategist, and I'm based between Dubai & Cape Town currently. The rest of my team are also based between either UAE or South Africa and includes a developer, designer, social media manager and PPC specialist.

Why did you decide to start working remotely rather than in an office?

I had initially run my digital marketing agency from Cape Town so I was already working with incredible talent over there -- once I launched 'Boguslavsky & Co' in Dubai, it made sense, financially, to run a lean business, working with talented people back in South Africa so I could offer my clients high quality services for a fraction of the costs that other agencies charge in the UAE.

How do you keep everyone feeling connected?

I've used Slack in the past, along with Google Docs, and, of course, Skype. There actually isn't that much overlap between the team members on projects -- it's more about us having a streamlined working process where everyone is aware of their own responsibilities and deadlines.

What are the biggest challenges you face working remotely and how do you overcome them?

The [lack of] face to face interaction -- really makes a difference to feeling like part of a real, cohesive, united team. I was recently in a city where my social media manager is based and we ended up having a business meeting over champagne and cheesecake, which was just so lovely.

The most important aspect of working remotely as a team is being able to trust your team and depend on them.

You're not just remote, but also what people might call a "digital nomad" -- working from numerous locations while traveling. What unique challenges does that lifestyle present?

It's challenging when you come to the point of wanting to settle down, have your own home, never hop on another flight again, etc., etc. -- I feel weird when asked for my address because I don't actually have one! We're in the process of changing this but I will definitely miss the digital nomad life.

With team members spread out and clients also in multiple places, how do you manage communication between team and clients? Do you ever wish you just had an office where you could get everyone in the same room at the same time?

YES. ALL THE TIME. But then I remember how much I always despised any kind of office politics and how I treasure living a different kind of life, and I'm actually quite happy with how I've structured my business.

So that's interesting. I've heard that a lot, actually, about remote teams leaving office politics behind. What do you think causes that to happen? Why do people seem to play fewer political games just because there aren't any physical walls around them?

I think office politics disappear when working remotely because the nature of office politics has to do with certain physical cues and dynamics of people interacting face to face; when not seeing each other daily and interacting mostly on email only most negative interactions almost dissipate in a way. People tend to focus more on work and less on political games because, 1) no one is observing them the way this usually happens in a physical office, and 2) the nature of remote work is almost solely on productivity, so no one wants to waste or spend time on anything beyond that, really.

What do you look for in an ideal remote employee? Are there any qualities that make someone more successful at working remotely?

Oh yes. Trust and reliability. More important to me than a specific skills set or knowledge/experience.

Describe your personal work environment.

I prefer to work from coffee shops -- the buzz around me, strangely enough, makes me focus and work more productively than anywhere else, even my own home office.

What are some of the tools you couldn't live without as a remote company?

Slack. Skype. Google Docs. Google Apps for Business. Hootsuite. Socialbakers. Trend Watching.

What advice would you give to a company heading down the remote working path?

The most important aspect of working remotely as a team is being able to trust your team and depend on them -- without that, you will not succeed.

As David Horowitz says in the interview below one of the most important things that a remote team needs to nail to ensure success is, "Communication, communication, communication."

One of the key pieces of the agile software development process is the restrospective -- a post-iteration meeting in which team member identify what went right and wrong and how to improve going forward. Yet Horowitz found that many distributed agile development teams weren't running retrospectives. This key part of the agile process wasn't being done and their work was suffering as a result. These teams were failing to communicate at the most important part of the process.

So Horowitz co-founded Retrium, an app specifically designed to help distributed agile teams run effective retrospectives. Not only that, but Retrium itself is a distributed agile team. Read on to find out how Horowitz approaches working remotely and why he believes distributed teams are the future of work.

Tell me about Retrium and what you do there.

Retrium gives distributed agile teams the ability to run effective retrospectives. It provides a set of prebuilt retrospective techniques (like Mad Sad Glad, 4Ls, and Start Stop Continue) which are just a single click away. I’m the CEO of Retrium and a cofounder. Since we’re a very small startup, my role is everything from taking out the proverbial trash to setting vision, from writing code one line at a time to talking to customers, and everything in between!

How many people are at the company now and how spread out are you?

At the moment, it’s just two of us. On any given day, we could be working from home, from a coffee shop, from a farm, or from the beach. We rarely work in the same physical location, and ability to choose your work environment is very liberating.

What made you decide to build a company specifically for distributed teams?

It’s really a strongly-held belief, based both on intuition as well as on data, that “work from anywhere, at anytime” is the future of work. I truly believe that what we call “remote work” today will simply be called “work” within the next 20 years. I wanted to enter the market today before that becomes obvious.

What do you think will be the biggest driver of that transition?

It's hard to name a single factor because it's really the convergence of multiple things at once that's going to make the transition possible.

First, you have the internet. Twenty years ago it was new, it was slow, and no one had it. Today, it's available in every city in the world and comparatively, it's quite fast. In twenty more years? My bet is that we'll have globally available wireless internet at speeds faster than our connections are at home today.

On any given day, we could be working from home, from a coffee shop, from a farm, or from the beach. We rarely work in the same physical location, and ability to choose your work environment is very liberating.

Second, you have a generational shift. For most of the 20th century, the ideal job could be summed up in a single word: stability. Your goal was simply to keep a stable job so that your family could have a modest living. Today, stability is generally not the goal for 20 and 30 somethings. We're taught to follow our dreams, to enjoy what we do. Life's too short. As the younger generation makes up an ever-growing percentage of the workforce, more and more working-age adults will have personal autonomy and independence as their goal. If you take those two trends together, faster and more widely available internet alongside a desire to pursue your passion, you'll see people wanting to work from wherever and at whatever time they wish.

How do you keep everyone feeling connected?

Communication, communication, communication. Look, 20 years ago if you had a distributed team, your options for communication were very limited. Today, technology is giving us the ability to feel more and more connected over vast distances. The problem lies not in the technology itself, but in its misuse and underuse.

My cofounder and I use Sqwiggle, Google Hangouts, and other video chat software to talk not just about work, but about everything else too. Asking “what did you do over the weekend?” and actually caring about the response makes us feel connected.

What are the biggest challenges you face working remotely and how do you overcome them?

Since we are a small company, there are times when each of us is intensely focused on a separate task. If one of us is taking longer than imagined to complete the task, it’s easy to assign blame rather than have empathy. I think that’s because there’s a lack lack of visibility into the minutiae of the other person’s day. When you’re in the same physical office location, it’s easy to tell that someone is hard at work and needs to focus, if the person is in a good or bad mood, or if the person is slacking off. Remote work makes this more difficult.

That's a really interesting point. Is there anything specific you do to make sure you and your cofounder keep on top of that mental accounting and always know where each other stand?

Absolutely, though we're not perfect at it yet! We've found Sqwiggle to help. It's an interesting product. Unlike traditional video chat software that requires a lot of upfront work to get started (installs, invites, etc), Sqwiggle is a quick and easy live video board of your team that's very simple to setup.

The reason it helps us keep track of each other is that you can automatically initiate a video chat anyone on your video board at any time ... even without their consent. Sounds scary right? At any point in time, anyone from your team can peer into your working space without you giving them permission to do so. But if you think about it, this is no different from the office environment. Have an office? Anyone can come in at any time. Work in open space? Everyone is always there by default. Sqwiggle helps to recreate that sense of togetherness in a distributed context. It has its pitfalls for sure, and like any tool it can be abused, but used correctly it helps us feel more together.

What's the biggest benefit that working remotely has provided for Retrium?

It’s simple math. I used to commute one hour a day, twice a day, to get to and from my office downtown. Now that I can work from home, I’ve reclaimed those two hours every day. I can use that time to improve the quality of my life (going for a run, spending more time with my wife, or cooking dinner, for example), or I can use it to work longer hours. Either way, two hours a day is ten hours a week and forty hours a month. That’s a lot of time.

If you take those two trends together, faster and more widely available internet alongside a desire to pursue your passion, you'll see people wanting to work from wherever and at whatever time they wish.

Do you think you lose anything by not having daily face time in an office?

Of course. But then again, everything you do in life has advantages and disadvantages. It’s a matter of weighing the costs against the benefits and deciding what works best for you. Certainly by not working in an office, you lose the water cooler conversations, the random lunch dates.

What do you think is the most important thing a distributed team can do to ensure successful collaboration?

You can’t just be distributed and hope to for the best. You have to focus on being good at being distributed. Like anything worth doing in life, it’s hard.

To me, the most important thing you can do to successfully collaborate on a distributed team has nothing to do with tools or process. Just like for a collocated team, success is largely dependent on relationships, teamwork, and culture. Work on building friendships with your colleagues, have empathy for them, tell jokes, and build a cohesive culture that everyone buys into, and you’ll be fine.

Describe your personal work environment.

It varies from day to day. When my family is out of the house, I work from home because there aren’t too many distractions. When my family is home, I’ll leave and go to a local coffee shop. At home, I have a dual monitor setup. That’s really important to me. I like to do my calls with leads and customers from home because it’s very quiet. At the coffee shop, I bring headphones to block out the noise. On the other hand, it’s nice being in a social environment.

How do you manage work/life balance when working from your home?

I know this is an issue that a lot of people struggle with -- I’m fortunate to not be in that situation. I love what I do. I’m 100% passionate about it and focused on it when I’m home. In the past six months, there have been a total of two days when I haven’t felt that burning desire to build the best retrospective tool in the world. That’s not a bad percentage of days! But I also have a rule -- when the kids come home, I’m 100% focused on them through bedtime. The only thing more important to me than my company is my family. I want to be a good husband and dad. That’s really what life's about.

What are some of the tools you couldn't live without as a remote company?

Finally, the tools questions! It’s interesting -- usually this is one of the first things people ask me. But as I mentioned earlier, to me it’s one of the least important aspects of being good at being distributed.

You can’t just be distributed and hope to for the best. You have to focus on being good at being distributed.

There are an abundance of tools out there to make your life easier as a remote worker. We use some of the obvious ones -- Slack, Trello, Google Hangouts. But we also love Sococo. Sococo tries to simulate the office environment by providing a office layout which you can put your avatar on. We really love it. We also use Sqwiggle and appear.in for video chat. Lastly, we use Calendly as a meeting scheduler. It ties in with our Google Calendar and it’s saved us countless hours.

What advice would you give to a company heading down the remote working path?

Before deciding whether to be distributed, ask yourself why? What’s your goal? Is it to cut costs? To gain time in your life back? To hire the best talent, regardless of where they live? Figure out what you’re trying to achieve and focus on it. You can’t do everything right the first go around, so figure out what’s most important to you and work to become the best at it. If you do that, I can almost guarantee you won’t regret your decision!

Under30Experiences (U30X) curates unique travel experiences in exotic locations specifically for young adults.

It's not surprising that a company that sends its employees on trips around the world would embrace remote work, but it makes even more sense for U30X given their focus on the millenial generation. (Remote work is an option that 68% of millenial college grads seek from jobs.)

Cesar Romero, an Experience Instigator, talks to Pajamas about how U30X is building a distributed company to deliver group trips all over the globe.

Tell me about Under30Experiences and what do you do there.

Under30Experiences is a travel company making traveling more accessible to young adults and helping them create meaningful relationships. It’s a community first, then a business.

My role with Under30Experiences is two fold. When I’m running trips, I’m the trip leader; when I’m behind the desk, I take the role of community manager.

How many people are at the company now and how spread out are you?

The two founders, Matt and Jared; Matt is currently in Costa Rica and Jared in Austin, TX. Our resident photographer and videographer, Courtney (currently in Ireland running a trip). Our other trip leader, Eric (currently in Ireland running a trip with Courtney). We have a virtual assistant Ria from the Phillipines. And I'm currently in Costa Rica for the next four months.

Has Under30Experiences been remote from day one? What made you decide to start building a remote team?

Yes we have been remote from day one and it was part of the vision when the company was founded.

Flexibility and work-life balance are extremely important to us and we wanted to have a global team capable of leveraging the power of today’s technology and execute from anywhere.

How do you keep everyone feeling connected?

This is something that we haven’t really mastered internally and we are constantly coming up with new ways to stay and feel connected.

It’s definitely a challenge when the whole team is spread out and 50% of the staff is out there running trips in remote parts of the world.

The internal communication channels right now are a combination of email, Slack, Skype.

For the community, we use Facebook Groups and meetups in different cities across the U.S. organized by members from the community.

What are the biggest challenges you face working remotely and how do you overcome them?

Definitely communication, face-to-face interaction, and creating that feeling of “connection.” We overcome this by constantly communicating via email, Skype, Slack, video, voice recordings, etc.

We are working on incorporating yearly team retreats because we have seen what it does in creating a stronger and more cohesive team.

What is the biggest benefit that a distributed team has afforded your company?

Flexibility and work-life balance.

You can work from anywhere as long as you get things done and get results.

Is there anything you think you miss by not working in an office every day?

Not really.

If I don’t feel like socializing, I can work from home. If I feel like getting out of the house, I can go to a coffee shop and work from there.

What do you think is the most important thing a distributed team can do to ensure successful collaboration?

Communicate everyday evaluating what worked, didn’t work, and what can be improved for the next day.

It’s a simple exercise but works wonders!

How do you make sure everyone at the company is in a good place, both mentally and operationally? What indicators do you look at to measure this?

We only have one indicator: Happiness.

If you are not happy and not having fun with what you are doing, it’s going to affect your performance in every aspect of your life. We definitely don’t want that happening.

We encourage everyone at the company to always be open about this and share what’s working and not working for them.

What sort of culture does your company have? Is it harder to build cohesive culture when you're so spread out?

We have a culture of putting people first; putting the community first.

The internal culture is very laid back where we encourage everyone to bring their true selves. We all genuinely like each other and it’s something that we are very proud of. How many people can say that they get along with their co-workers, bosses, etc?

There’s a challenge in building a cohesive culture when you are spread out, but with constant communication you can definitely mitigate this.

We have all been on trips together and this really helps because the shared memories of these trips help us out in carrying that feeling of camaraderie over until the next time we meet in person.

Describe your personal work environment.

On most days I work from home and I love it!

WiFi, comfortable chair and table, instant access to a full kitchen, paintings on the wall, and precious quietness. You can’t beat that!

Except when it’s too quiet or it’s such a beautiful day outside that I just can’t help but to get out and go to a coffee shop and work from there.

How do you manage work/life balance when working from your home?

The first hour is a “power hour:” brush teeth, shower, breakfast, reading, journaling, take the trash out, bulletproof coffee, exercise.

The last hour before going to bed is also a “power hour” where the most important thing is to think about the most important task that needs to get done tomorrow.

The mornings are usually for marketing and sales strategy and the afternoons are a mix of emails and engagement with the community.

How do you keep distractions to a minimum? How do you personally measure efficiency?

Distractions are always there but the one thing that really helps me is figuring out the night before what needs to be done first thing in the morning... after my power hour of course. :)

If I get that one thing done by the end of the day, then it was a productive day.

What are some of the tools you couldn't live without as a remote company?

• Gmail
• Google Docs
• Skype
• Slack

Very simple but it works.

What advice would you give to a company heading down the remote working path?

Create a vision for your company and the type of culture you want to create.

Evangelize your team on this vision and keep a constant flow of communication.

When Josh Thompson wanted to move out to rural Colorado with his family to be closer to the mountains he loves to climb, he knew finding a company that allowed him to work remotely would best suit his desired lifestyle. Luckily, Thompson found Litmus, a Cambridge, MA-based email marketing tools company that operates at least 50% distributed.

Thompson talks about the advantages of remote work for Litmus, how the company keeps everyone in sync, and why remote work works so well for him in the interview below.

What does Litmus do and what is your role there?

Litmus is a software company and we build tools to help our customers build, test, and track emails so our that person can spend less time building emails (it’s a surprisingly difficult thing to do well) and build better, more effective emails and campaigns. Our platform and analytics are used (via API) by notable companies like MailChimp, Campaign Monitor, Return Path, and many more.

I’m on the customer success team, so I handle inbound sales for our API, and handle all the renewals related to our annual accounts. Stuff moves fast at Litmus, so my job has (and will continue to) evolve, but that’s the simplest definition.

How many people are at the company now and how spread out are you?

About 42. Maybe 44? We hired four people in the last week, I think. [And we're still hiring] - ping me if you’re interested in applying. We’re always on the hunt for great people, even if there is not currently an open role. Oh, and we’re a 2014 Best Place to Work winner. ;)

Most of the remote employees are spread across the US, with another group spread across the UK, and individuals also in Canada, Ecuador, and Pakistan (one of our designers - he’s top notch).

What initially drew you to remote work?

Location independence. I started looking while living inside the DC beltway with an hour commute each way. I wanted to move to Colorado, and knew that remote work was the best way to make that happen. So I started looking for any and all remote job opportunities, and am thrilled to have found Litmus.

How does Litmus keep the ~50% of the company that's remote feeling connected?

Many things, but here are a few of the big ones:

1. All company communication is in Slack, Basecamp, Trello, Bluejeans, etc. Even the Boston office is often mostly empty, because so many staff work from home, so the default communication style assumes everyone is remote.

2. At least twice-a-year company meet-ups. We host an annual “Email Design Conference” in August, and an annual company meetup/retreat in March. Occasional smaller get-togethers sprinkled in, and I usually see at least a few people that I work with every three months.

3. Big company events often take place in giant video calls. Every potential hire does a “meet the team” call, where we bring them into the Boston office for a day (even if they’re flying in from quite far away) and then the entire company can jump on a video call with them. Our twice-a-month company meetings usually take place with everyone in front of their computer, even for the folks in the Boston office.

4. The company was founded with remote work in it’s blood. Two of the three cofounders moved from London to Boston ten years ago to grow the business, so before they’d hired even two people, half the company was remote.

The office in Cambridge, MA sounds like an awesome place -- catered lunch and free snacks, weekly happy hour, regular parties and outings, is there anything that Litmus does to make the remote members of the team feel more included? How do you avoid creating a "two-tiered" culture on the team where remote folks feel separate from their in-office colleagues?

The office is pretty sweet, but even the staff in Boston often work from home. As you can imagine, traffic (even in good weather) is terrible, so there is a blanket “work from home whenever you want, but try to make it in every other thursday for company meetings if you can” policy. I.e., even us remote staff are usually in the exact same bucket as the non-remote staff.

Also, we don’t have an open-office floor plan. Most employees have their own office, or share it with one other person. This further ingrains the text-based communication.

We all live balanced lives, so when we’re at work we work hard to get shit done, but then we go home and do other stuff.

Litmus goes all-out to make sure the remote staff have the same tools as in-office. Every employee gets top-of-line hardware, external monitors, and a good desk chair (if they don’t already have one.)

I’ll admit, sometimes I wish I could participate in some of the parties they throw in the office, but after I take my five-second commute to the other side of my living room, and grab my gear to head out rock climbing in Colorado, I don’t miss being in Boston too bad.

How would describe the company culture at Litmus? Is it harder to build cohesive culture when half the company is spread out and the other half is in one place?

Culture is extremely inclusive. We’re growing quickly, so those questions will inevitably stay top of mind, but again, because the remote work policy is so ingrained even in the home office, we are all functionally working remotely. (Some days there are only two or three people in the office. Last winter, there would be weeks where NO one made it into the office!)

As far as cohesive culture, I think the average age at Litmus skews a bit older than what may be assumed for a software company (plenty of our employees have kids) so there’s not much of a “go-out-for-drinks-after-work” attitude, anyway. (Except when the whole company is together in Boston for our conference. That week has much more drinking than normal.)

We all live balanced lives, so when we’re at work we work hard to get shit done, but then we go home and do other stuff. It’s very professional, and very friendly.

Do you ever feel like you lose something because you're not working in the office every day?

I’ve lost my commute, and I do really enjoy the casual conversation that happens around lunch or when walking around the office, but I don’t think I’m missing anything irreplaceable, or that cannot be had in a remote work situation.

Personally, what are the biggest challenges you face working remotely and how do you overcome them?

There are certainly challenges.

1. I thrive off of external affirmation, and I love being able to show how hard I work. In an office you can be the first one in and last one out, but, besides not being healthy, that doesn’t actually correlate with getting work done. So, because I can’t telegraph how hard I work, I have to show how much I get done, but sometimes (often!) I don’t feel like I’ve gotten as much done as I had hoped. Projects grow in complexity, or I’ll have spent half the day on the phone.
   
   So, I’ve had to set up fairly regular official performance evaluations with my manager, just so I convince myself that I’m actually doing good work. So far, all those reviews have been extremely positive, but I always have a sneaking suspicion that I’m failing somehow. This is specific to me and my disposition, so everyone reading this is either nodding along in understanding, or cannot understand this at all.

2. I don’t have external signals/environments that signify “work time.” I have to rigorously control my work environment so I can get in the zone and work well. I use a mix of writing down my projects for the day (and the things I’ve accomplished) to keep me on task, using a Pomodoro app to work in chunks, and sometimes SelfControl to kill Reddit/Hacker News/Twitter to help avoid those distractions.

3. I don’t have those signals that signify “not working.” I don’t have a commute home to think about work or other things. I just type in Slack “heading out, have a good night.” and... work is done. Sometimes I’ll take a walk, but sometimes I just try to jump right into prepping dinner or doing non-work stuff. If work was stressful, this stress carries over to home. My wife is really good at identifying if I’m a little off and helping me decompress.

On the other hand, what are the biggest benefits to working remotely?

Phew. So many.

1. I don’t commute anymore. There’s two hours a day back. (And a lot of gas and money in maintenance.) I was stuck in traffic earlier today (on a weekend) and was so frustrated by it. I don’t ever have to deal with rush hour.

2. My wife and I now own only one car. That saves a lot of money.

3. We moved to Colorado. I loved every minute in Colorado.

4. Our landlord wanted to move into our apartment, so we had to leave, and my wife stopped teaching, so we headed to Buenos Aires for two months, then have been traveling around the east coast, following the climbing, and spending time with dear friends.
   
   We spent three weeks working in rural West Virginia, and I’d enjoy world-class climbing after work and on the weekends. I’m about to drive to Kentucky for more world-class climbing for three weeks. I used to drive between six and eight hours on the weekend to do this. Now I just drive 3 mins to the rock. Rent is cheap out in the boonies, too.

5. My work is made more effective. Without all the office politics and micromanaging that infects most offices, I have tons of responsibility and freedom to do the best job I know how to do, and to experiment a lot with how to make things even better. This speaks as much of working remotely as it does of the specific culture of the leadership team at Litmus, but they go hand-in-hand. If you cannot trust your staff to work remotely, you won’t trust them in an office either. If you can trust them to work remotely, you’ll trust them to do good work without you breathing down their neck.

What do you think is the most important thing a distributed team can do to ensure successful collaboration?

I love meeting the team in person (or, when we add someone to the team, I’ll catch them on a video call for 20 or 30 mins just to talk and get to know each other). Knowing the personality and lives behind that little profile picture on Slack makes the communication so much richer. We all have inside jokes, memes, and a rich history of communication that makes the more context-free text-based communication work.

So, time in person is even more important when you work remotely. I think. But I’m not wise enough to know The One Thing (TM) that matters.

What are some of the benchmarks Litmus uses to make sure the team is in a good place, both mentally and operationally?

I meet weekly with my manager to make sure I’ve got all the tools and resources I need for whatever projects I’m working on.

We have flexible work hours, and generous paid time off policies. (If we went with “unlimited” vacation time, no one would take enough time off, so instead we get about six weeks paid vacation off a year, and it doesn’t roll over, so you have to use it.)

Every new employee gets new top-of-line hardware, monitor, peripherals, and anything else we might need. We all have company cards that we’re encouraged to use as needed. I’m not hampered by a lack of tools or equipment or rest at all.

Are there any specific qualities that make someone more successful at working remotely?

The same qualities that make someone successful in an office apply to working remotely. You’ll need to be a “self-starter,” and have a lot of initiative. I think a good proxy for both of these traits is side-projects, or side-hustles. If two people are equally qualified for a role, but one of them has a good side project/hobby that they’re passionate about, they will get the job. The primary reason I got my current job was because I had side projects (aka “public proof”) that demonstrated my drive and initiative.

I don’t have someone breathing down my neck to get work done, so for better or worse, I alone am responsible for the work that I do.

PS: I know it can be discouraging to read something like that, so if you just said to yourself “well, of course its easy to get a job with a cool side project” here are two “words of encouragement:"

1. Your side projects do not need to be beautiful and graceful. Some of my side projects are ugly as sin: http://joshworks.site44.com/, others less so: http://climbingweekly.co/, http://josh.works/

2. You don’t have to have a side project to have a side project. Just say “My hobby is finding a hobby” and start documenting your search for something worthy of your time and energy. For example, mine could be:
   
   Josh’s Quest for a Side Project: How I found something interesting to work on
   
   Or
   
   Josh’s Epic Quest. See Steve’s Epic Quest or Jia Jiang’s 100 Days of Rejection for inspiration.

Describe your personal work environment.

In flux lately. For most of my time at Litmus I worked from a standing desk in my living room. I had an Apple Monitor, laptop stand, comfortable chair, etc. My wife and I have been “nomadding” these last few months, living out of our car, a few weeks at a time in a different place. So currently I’m down to just my laptop, no mouse, no external display, etc. I was on an ultra-minimalist kick for a while, but I think I’m ready to reintroduce a mouse and external keyboard into my life.

That’s the physical environment. Anytime I open my computer, I feel very at home. I have my machine quite configured to my liking, and I work well on it.

Here’s some key tools that make MY machine feel like home, and allow me to work in really any environment.

• TextExpander (Stop typing the same thing over and over. I’ve used it over 30,000 times in the last 18 months.)
• Alfred (Workflows are addicting. My dashboard tells my I use it on average 50 times a day!)
• Seil (To remap CAPS LOCK KEY to delete.)
• Flux (Save your eyes when in a dark room/late at night/early in AM.)
• PomodoroOne (Do more in bursts.)
• Toggl (Figure out how you spend your day.)
• RescueTime (Track how much time you spend on “productive” parts of the web vs. unproductive.)
• 1Password (Save time, be more secure online.)
• Bartender (Have a clean menu bar.)
• CloudApp (Share stuff easily.)
• Skitch (Take and annotate screenshots.)
• PIA (VPN, quite cheap for a year. Make you/your company safe when using public wifi.)

How do you manage work/life balance when working from your home?

Sometimes I manage it poorly. It’s easy to spend all day working, but when you do that, your efficiency goes way down. It’s hard for me to sometimes keep work to JUST those “normal” work hours, but it’s important for my own health and recovery to do so. My wife is really good at helping me see when I’m working too much.

The same qualities that make someone successful in an office apply to working remotely. You’ll need to be a “self-starter,” and have a lot of initiative.

I am a very active rock climber, and usually climbing helps me balance my work. If I have told a friend I’ll meet him at a certain time at a certain place, I have a hard stop on my work, so it forces me to be extra efficient so I can stop at the appropriate time.

How do you keep distractions to a minimum? How do you personally measure efficiency?

I do a few things to stay focused. The easiest is to work in blocks. I love the Pomodoro technique, and try to fit my work into those 25 mins work/5 mins rest cycles. Invariably, something “breaks” the cycle, but a lot of work gets done in a few of those.

If I’m finding myself procrastinating, that’s usually an indicator that I need to break the work into smaller pieces. Large tasks are overwhelming, but less so when broken into small pieces.

I usually start my day with a notebook and a few minutes of thinking about what I want to accomplish for the day. I’ll then gear the pomodoros towards accomplishing those goals.

What are some of the tools you couldn't live without as a remote company?

Slack. Bluejeans/some sort of video calling tool. Basecamp, Trello, Google, Github. Two factor authentication.

What advice would you give to a company heading down the remote working path?

If you’re thinking about “testing the waters”, you need to give it a fair shake. “Test” for a long time, and with all your employees. At least a month or two to iron out kinks, and plan on spending money.

When Litmus officially tested remote work for even the in-office folks, the company had to buy laptops for some employees, and a bunch of external monitors. We use the Apple Monitor, so that was probably at least $10-15k invested in the “experiment.”

The experiment worked out great, and this last winter when Boston (home office) was crushed by 120 inches of snow, work continued uninterrupted, even though roads and public transportation was almost completely unusable.

That $10-15k equipment expense resulted in three months of the entire company moving at full efficiency, rather than grinding to a halt in a really busy time of the year. Maybe the best investment we ever made!

In January 2014, Kate Kendall launched CloudPeeps, a marketplace for freelance community, content and marketing professionals. Just under two years later, CloudPeeps now has over 100 customers and has received over 2,000 freelancer applications. She also runs an email newsetter, The Fetch, which serves work-related content and event listings to over 30,000 subscribers.

Both companies are fully distributed and Kendall has become something of a remote work evangelist on Twitter. Below she shares the story behind The Fetch and CloudPeeps, what drew her to remote work, and what it's like to build and manage a pair of successful distributed companies.

Tell me about CloudPeeps and The Fetch and what do you do there.

So, I had the ideas for The Fetch and CloudPeeps around the same time in 2011 when I was living in Melbourne, Australia. The Fetch was a way to curate all the great professional-geared events happening in one guide (a weekly email digest) and CloudPeeps originally started as a service that connected startups and small businesses with remote community managers.

After bootstrapping The Fetch for a few years full-time and struggling to find and manage the right freelancers to help me grow my business, I came back to CloudPeeps as a way to solve this problem. In January 2014, it launched as a talent marketplace that matches businesses with top freelance marketing, content and community pros.

My role as an early-stage startup CEO varies greatly – I work across everything from product to operations, sales to content, fundraising to community building.

Your Twitter bio describes you as a lover of "remote work culture." What initially drew you to remote work?

When I was finishing up my college degree, I always had this approaching dread of working 9-to-5 in an office. When I did start my first full-time job, I'd spend 45 minutes commuting one way to then sit in a windowless, open plan, grey office. I found it all very inefficient, unproductive and exhausting. I always felt like I could achieve more in a flexible environment.

At first, I wanted the freedom just to work a bit later – or even go to the doctor or post mail during business hours. Then I started seeking freedom to travel and pursue personal projects. All this led to me selling a lot of belongings and becoming a digital nomad for a few years. Now, I love that remote work is mainstreaming with numerous companies working this way.

Your companies operate with a fully distributed team. How many people are there total and how spread out are they?

Right now, I'm working with eight people remotely – we have the majority of the team in San Francisco, then there are folks in Brooklyn, Orange County, Berlin, Toronto and Rome!

How do you keep everyone feeling connected?

Slack has honestly changed the nature of work forever. Even when I visit a large tech company's office, I notice everyone is communicating via IM and the emphasis is less on in-person conversations. To keep connected, we host an all-team weekly standup via Google Hangouts on Mondays, then I do direct synchs with different teams throughout the week. We also have an active and well-organized Slack channel (make the most of integrations), and use Asana, Trello and Github to monitor projects. Another thing we do is biannual team retreats where we all get-together for some face-to-face time. We're still a growing startup, so we don't go to far-off places like say, the Buffer crew does! We've been to Lake Tahoe and Santa Cruz so far.

What are the biggest challenges you face working remotely and how do you overcome them?

Some of the challenges of remote work can also be seen as benefits. For instance, I think it's really easy to tell who's performing and who isn't in a remote team – as well as who really gets what you're trying to achieve in your business, and who has been a bit distracted or less focused. So much of remote work is about productivity and communication – you'd think it'd be easy to hide working remotely but it isn't. Setting clear goals, milestones, deadlines and a task owner along with lots of planning is key. We do monthly one-on-one feedback sessions to make sure we stay on the same page.

I'd spend 45 minutes commuting one way to then sit in a windowless, open plan, grey office. I found it all very inefficient, unproductive and exhausting.

What is the biggest benefit that working remotely has afforded your company?

The biggest benefit is that it's attracted the right kind of people to CloudPeeps. We have a diligent, humble, productive and kind group of folks on the team. We do a lot with a little. We don't have the usual politics that you sometimes hear about in traditional offices: people masking other people's ideas as their own, never-ending meetings, questionable interactions to minorities, not leaving the office until after 10pm, crazy managers and so forth.

Another benefit is that we've been able to lessen our burn rate as we're not spending thousands and thousands of dollars on an office each month. Some tech companies are spending hundreds of thousands of dollars on offices each year, and I like that we can put more back into our business or salaries.

Do you think you lose anything by working remotely?

I think you lose a bit of the ability to set and control a team's pace working remotely. There's going to be some times when you need to work faster and hustler harder to meet goals, and it's easy to do that in person when you're side by side. That said, I think remote work creates a more consistent pace – it's like running a marathon or being an athlete – and there's less long-term burnout and higher retention.

What do you think is the most important thing a distributed team can do to ensure successful collaboration between team members?

Set the collaboration around an action item and goal. Often we think of collaboration as communication so the focus is on the communication rather than the action. We used to spend a lot of time communicating on Slack, which in effect is the same problem of spending too much time on emails. We switched our communication to be around Asana for non-tech tasks and Github for tech so that collaboration is always focused around a goal. We then have an #ideas channel in Slack and do some brainstorming over a Hangout to collaborate on items outside of the day-to-day.

So much of remote work is about productivity and communication – you'd think it'd be easy to hide working remotely but it isn't.

It can be difficult to build a cohesive culture across geography. Is there anything special you do to bring the team closer together (either physically or virtually) and nurture a unique dynamic?

Our team retreats have been great for bringing people together face-to-face. We've also just launched the Freelance Friday community as a monthly coworking meetup for creatives, entrepreneurs and independents, which allows our team to connect with their local community too. We also sponsor coworking memberships, so team members can get some people-time in when desired.

Describe your personal work environment.

I work from home in my sunny apartment in San Francisco. It's right near Chrissy Field and the Presidio, which was important for me as I wanted somewhere close to nature after living in New York for two years. I have one of those white IKEA Melltorp four-person dinning tables that I use as a desk. My external display and mouse pad is also white so I tend to opt for minimal and clutter-less environments. When I want to mix things up a bit, I work from my couch. This Byllan laptop desk was probably the best $15 I've spent! I'm trying to bring more plants into my environment. Another thing to note is that I rarely listen to music. I focus better and get more stuff done in silence! I use Leuchtturm1917 notebooks to jot down notes and clear my mind.

How do you personally manage work/life balance? Do you think that balance is harder to find without an office to go to every day?

I think my remote work experience and work/life balance would be different if I wasn't a founder or CEO. It's hard to have true balance regardless of having an office or not. You're constantly on, thinking about company growth or managing projects and people – if you've raised a round of funding, that also adds additional time pressure, responsibilities and expectations.

When I was working solo on my first company, The Fetch, I actually found balance harder though and would work 100-hour weeks. With CloudPeeps, I tend to take weekends off and encourage the rest of the team to not contact others (use a Gmail plug-in Boomerang or Streak to schedule emails for the week if you want to catch up on the weekend). I also do lots of exercise, including indoor soccer, barre, yoga, running, hikes and get plenty of sleep. ClassPass is great for accessing numerous gyms and studios on-demand.

What do you do to make sure you're operating at peak efficiency?

I track my time in RescueTime and look back on the weekly summary each Sunday to see where I spent my time and focus. I wish it would monitor my iPhone and calendar so I could get more of a complete understanding. Sleep is also very important to me – I tend to make sure I'm asleep by 12am now (coming from a 2-3am background) so I can get a good eight hours. Also, eating well. I'm pescatarian, don't drink coffee and alcohol rarely.

List some of the tools you couldn't live without as a remote company.

We use an insane amount of cloud services as a remote company: Slack and Google Apps for everything, Asana and Trello for project management, Github, Heroku, AWS and Bugsnag for development, Help Scout for happiness and our knowledge base, Xero for accounting, Buffer for social media posting and analytics, Campaign Monitor and SendGrid for email, Justworks for payroll, Stripe and Paypal for payments, 1Password for password collaboration, Baremetrics for SaaS analytics, HelloSign for legal signatures, Twitter Bootstrap for easy prototyping, and so on.

What advice would you give to a company heading down the remote working path?

I know a lot of larger tech companies who have a combination of both now but I'd say pick one or the other. Especially if you're early-stage. Around six months in we were trying to do both at CloudPeeps and it wasn't working out – our team culture felt split and people were confused. When we made the decision to embrace being fully remote, things fell into flow faster.