Josh Thompson - Litmus - Remote Work Interview

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:

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.
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.
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.
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.

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.
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.
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.

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.
My wife and I now own only one car. That saves a lot of money.
We moved to Colorado. I loved every minute in Colorado.
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.
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:"

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/
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!