Sten Tamkivi - Teleport

A company like Teleport probably wouldn't have existed 10 or 15 years ago. The rise of tech startups and the emergence of robust online communication tools means millions of people have shifted from the office to "work from anywhere" over the past decade. Millions more are expected to follow over the next few years as more of our work involves manipulating bits of data instead of physical objects and place matters less.

Teleport makes tools for this emerging, globally distributed workforce. Their growing suite of tools helps a new breed of startups coordinate meetings, plan travel and find the best place to live. Naturally, Telelport itself is a globally dispersed team. Here's CEO and co-founder Sten Tamkivi on building a company in this new era of work.

Explain what Teleport does and your role there.

Teleport is a Place Scout for Startup People. We build software for people creating tech companies (as founders or employees) to find the best place to be for what they need to do: reduce cost to extend their runway, find like-minded people to build with, be closer to clients, land in a tax and regulatory environment with least friction, and so forth.

We have launched three products launched this far:

• Teleport for Startup Cities -- discover and budget your next move around 105 startup-friendly cities
• Teleport Flock -- discover and budget the next meeting of your distributed team anywhere in the world
• Bay Area Teleport -- find affordable and commute-optimal living around Silicon Valley (to be expanded to other urban areas)

I am one of the three co-founders (with Silver Keskküla and Balaji Srinivasan), as well as the CEO of the company.

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

Teleport is today a team of 10 full time, and we have a few freelancers and interns who are spending a large share of their time with us, especially in the summer.

We are running a fully distributed team in 6 countries: Estonia, US, Germany, Switzerland, UK & Ukraine + my co-founder Silver is roaming as a full nomad in places like Colombia and Galapagos islands most recently. We are spread across 10 timezone hours (Palo Alto to Tallinn/Kiev) and try to stay in those bounds for now. Our team speaks English, Estonian, Russian, Ukrainian, German and Spanish. And just a little bit Chinese and Japanese.

What led you toward hiring a distributed team for your company? Many of Teleport's core team previously worked on Skype, a favorite tool for connecting remote workers. How did your experience at Skype influence your approach to building Teleport, both the product and the company?

The Skype roots that half of our team share are definitely a huge part in both what we are building, as well as how are we doing it. Basically, if at Skype we were making the world a smaller place in metaphorical sense, virtually, at Teleport we are getting to the next stage and moving people around physically.

At the same time, Skype was a super distributed organization -- by the time we got to 200 people we were already spread across 10 locations and 16 timezones. I guess we just thought that building what we build, free communication tools, we don’t have to be in the same room - so why limit yourself.

Compared to traditional office environments, do you think you lose anything working remotely? What do you gain?

I really love working in an office with high quality hifi equipment, streaming ambient beats in the corner. That is hard to replicate with headphones in a cafe or co-working space, even when we have published our Tallinn office playlist on Rdio to the entire team to enjoy and contribute to. And I think there is more to this music example in metaphorical sense -- in any remote setting you easily loose the most ambiguous kinds of communication first, the serendipity and the subtle sense of being together and building together. Being remote it is easy to agree on written report formats, and much harder on the little cultural rituals and elbow nudges.

If at Skype we were making the world a smaller place in metaphorical sense, virtually, at Teleport we are getting to the next stage and moving people around physically.

That same sense of physical togetherness is of course a cost or even a distraction on its own. So a big benefit of remote work is a cleaner separation of communication vs. individual work (or, your maker vs. manager schedule, to quote Paul Graham). Many people, especially in engineering and creative roles, confess they become much more productive when they have more individual “maker” time in uninterrupted blocks, from which they only consciously surface to interact with the team. I believe this is true, but you have to master extracting all the inputs and opinions from your team in those condensed communication windows -- whereas in a single office you could just walk over to their desk 8 times a day to clarify your next question.

What is the most important thing your team does to ensure successful collaboration across geography?

If I have to pick the single most important thing, I’d say: being smart about picking the communication modalities to discuss different problems, from a quick Fleep chat ping, to Speak.io calls (slowly replacing Skype & Google Hangouts in our team) to getting on the plane.

And I do think the fun tone & some jokes in our Watercooler group chat come close in importance.

Talk a bit about the culture you're building at Teleport and why that's so important to the success of the company.

I strongly believe that in order to build products that people love around the world you have to mimic your userbase. You can not isolate 2 Estonian males in a room in North-Eastern Europe and expect them to build something that the males and females, young and old in US, China and South America will enjoy. To understand what people want to you have to have a lot of empathy, get out of your comfort zone and invite others from varied backgrounds to join you.

As a company we strive for a culture as fluid, diverse and borderless as the world we’re serving. We want to work with people who have intellectual curiosity and deep interest for varied aspects of life, the more eclectic the better. People who understand humans, people who understand machines and especially the rare people who know how to make the two work together. And most of all: if you are a bit of a nomad yourself, with an urge to live in new places and skills to continue working with the rest of the team while wherever -- this would be a team that really gets you.

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

Hiring remotely, to a large part, is about letting go. Letting go of your micro level control as a manager, your ability to direct and review everything. You just have to give people the freedom to run with the higher level objectives you agree with them, and trust their ability to make the smaller and bigger decisions on the way. So when hiring into a team like that you have to find people who are not only experts in the job you need them to do, but can raise up from that formal definition, have an internal drive to excel, sense of commitment, personal accountability, ability to make decisions quickly.

“Act now and ask for forgiveness later” principle helps remote teams much more than co-located ones, I believe -- and this is by far not a comfortable maxim to live by for everyone, especially more conservative people.

To understand what people want to you have to have a lot of empathy, get out of your comfort zone and invite others from varied backgrounds to join you.

A pro tip for distributed startups: over half of our early Teleport team have been founders themselves in the past. It does not mean they have had to be super successful with their previous ventures, but it is a great proxy to show that they have stepped up to a challenge of creating something of nothing in the past. And they are personally familiar with what the entrepreneurial struggle means, so they might understand what you as a CEO have to get done, even when they don’t see it every day next to you.

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

Operational bit is easier. We do set quarterly OKRs, discussing together what are the most important things we need to tackle and how to best measure them. And from there we are getting constantly better on how these top line objectives, as well as many more nuanced metrics building up to those become part of our daily metrics reports, Ducksboard dashboards, Heap reports, etc.

Mental health and energy of the team is much harder to surface via metrics, of course. Probably my weekly 1:1s with every team member are the most consistent channel to gauge that; a notable investment of time, but still something very important I intend to do as long as it is possible to scale -- and when we grow, ask my direct reports to continue the habit. And it is also about creating a culture where people feel comfortable speaking not only about their successes, but also raise their failures, concerns and doubts for an honest discussion with peers, rather than let them burn slowly somewhere under the surface.

What's your personal work environment like?

In my backpack you will find a 13” MacBook Pro, two pairs of headsets (Bang & Olufssen and Jaybird) and a Zoom digital recorder and mics for our freshly started podcast, Free People Move. I do have a bigger monitor in my home office, but tend to work mostly out of co-working spaces (Stanford StartX the most)

I look forward to spending more time in the only proper office we have in Tallinn, Estonia this summer; you know the kind where we have a door, a logo sticker on it and a whiteboard and coffee machine and stocked fridge inside. It is a completely different vibe to be in the same room with your team at times, and you learn to cherish it much more when you’re remote most of the time.

How do you personally manage work/life balance?

I am currently in an amazing place. Married a dozen years we have had time to work out this lifestyle with my wife we both enjoy. Her work as a journalist and writer is also quite location independent. Our older two kids, Gustav & Etta, are old enough to cheer along to what Teleport does (at 9 & 7) and we just had our third one, Eik, in December. I now highly recommend that to all aspiring entrepreneurs: when you start another company, also have a baby at the same time. This really sorts out your sleeping hours well!

“Act now and ask for forgiveness later” principle helps remote teams much more than co-located ones.

How remote work plays into the balance with family is twofold. First, my kids have now spent extensive time in 4 countries, speak Estonian and English fluently and hold a personal record of something like 10 flights of more than 5 hours long in a 2 month window. I trust they will always look at the world in a much more empathetic, humble and curious eye than they would have staying in any one place. As they say, “our home is where the family is.”

And at the same time, when I want and need to spend time at that moving home, I am way more flexible to pick my hours. We were just in our historic family summer home in the beautiful white June nights, on the island of Saaremaa in the Baltic Sea for the last week. I was still working 8-10 hours most days, accessible to my team while heating the sauna for the evening or sitting in a design review call on a Friday night with my 6-month-old sleeping on my lap. And when I close the lid of the computer, I’m there with my family 2 minutes later, every day, not just for a rare Sunday as many founders I know.

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

As teams working in remote setups so often discuss this topic, we ended up publishing an overview of our tools in a blog post. And for the more technically minded, our tech stack is public too.

Do you have any advice for a company heading down the remote working path?

Oh, there are so many things that you can get wrong (and luckily right, too, if this is not your first time around the remote working block) that I have started teaching a 90-minute workshop in some startup incubators on the topic of managing distributed teams. To pull just a few small things out as a teaser:

Our communication tech has improved vastly, but to date, you can create human connections only face-to-face, and then maintain them over (video) calls. Not vice versa. Let’s see where Oculus VR and other interesting advancements will take us, but still you need to have a good balance of being there and being remote.

The simplest framework I really like is one put forward by Jared Ponchot of Lullabot, who in turn borrowed it from the open source movement. He pointed out that successful distributed teams do three things well: write liberally, chat frequently and congregate occasionally. I think this is very well put, and I have tried to use these principles in hiring and management for many years.

And lastly, trying to become “a remote working company” runs the risk of becoming a little bit pregnant: you either are or you are not. It is not possible to successfully add a single remote working employee in to a tight team of 20 already humming in the same physical office. For any member of the team to be successful remotely, everyone else needs to adapt how they work -- replace watercooler conversations (we actually have a Fleep chat with that literal name, too) with chat messages, and write down even the mundane things they used to shout across the cubicles before.

So in that sense, it is even a bit easier to become distributed from day one, build location independence into the DNA of your company like we do at Teleport, than to attempt reforming existing organizations to this later. Start early, because the world is heading towards more mobility for sure.