Interview with Sondre Rasch from SafetyWing

by Adam
26 October 2020 - 6 min read

Please introduce yourself and tell us about SafetyWing?

My name is Sondre Rasch, I am the co-founder and CEO of SafetyWing.

SafetyWing is building  global social safety net. That means global health insurance, travel medical, dental and maternity for remote workers and digital nomads, as a replacement for national welfare systems they cannot access.

How did you start working remotely and why?

SafetyWing was remote since the founding. My former company SuperSide was also fully remote. In some sense I started working remotely back in 1999, when I as a teenager made a webhostinging company with some internet friends. Slack didnt exist yet, but we had something called IRC which worked the same way.

The internet is like a city, where you can find the most interesting and talented people. Because the internet is so much bigger, you can get much better matched and talented people there, compared to if you just hire in your local city.

Most importantly however I do find that it gives me and also the team more freedom and a better life. It is pleasant to not have to commute. And it is a lovely thing to be able to move wherever you want in the world, or travel when you feel like it, or go for a walk in the middle of the day.

Do you have a dedicated office space where you work from everyday?

Yes I do mostly work from home. I have a separate work place, like an office, in my house. The first years I worked remotely I didn’t work a separate place, because I liked to work from the couch. This was a huge mistake. When you work and relax at the same physical spot, the habits from either world spills over in the other. It is much easier to work without distraction, and fully relax when you do relax, if you do it in seperate physical locations.

I do however work from co-working space when I travel, which is quite often.

What are some of the cons of remote work?

The biggest one is that you have to be intentional about serendipitous information flow. I think the water-cooler chatter is really important. Here I think the best new ways to recreate this in remote is yet to come.

Two hopeful ideas that remedy this somewhat are workmates and “lunch”. Workmates like Focusmate, where you go on camera with a stranger, friend or colleague, not to talk but just to say what you plan to work on. And “lunch” is an half-hour we have before our weekly meetings meeting where there is no agenda and people can talk about anything.

How many hours per day do you do deep and productive work?

Ink it is usually in the 3-5 hours range. I have many meetings, but thankfully they are all clustered in the morning, so I have the afternoon to do deep work.

My favorite mechanism is to start the morning by asking myself what I need to do today, and what are the most impactful things I can do towards my most important goal or problem. I then write it down, and usually that alone is enough to make the day a lot more productive for me.

I also find it useful to get into a state. For me that is in the morning while getting ready I listen to something helpful, like a lecture concerning ideas, startups or philosophy. Every week we also state our top 3 goals for the week with the team, and say whether we got last weeks goals done. That is also a motivator that I find useful.

Lastly, the distraction almost all of us struggle with is the pull of social media and the internet in general. For that I use a tool called SelfControl to block it out during the workday.

What is your process to find and hire remote employees?

We always post to RemoteOK and Workew, which are sites dedicated only to people working remotely. We also share the post to our Angellist page, and typically also share the post to Hacker News, which is a benefit to having been in Y Combinator, as well as to YCs Work At A Startup page. The latter I find to be a particularly great source of candidates and several of our hires.

People apply regularly via email. We sort the applicants looking for authentic and interesting people that share our mission whom we book qualifying interviews with. Everyone also has interviews with the founders and the relevant team in a group conversation. Finally we do a real test task, like a micro-project, that is paid. We find this to be a really great signal of how someone is to work with, and it also tells them how we are to work with.

I’ve noticed most remote companies offer health insurance only to U.S based employees. Are you seeing more companies offering insurance to their international team?

Our impression is that the reason remote companies usually does not offer health insurance to international employees is because it is borderline impossible. Of the companies who do, the most common way currently is in the form of a stipend. For the few who do buy it, what they have is a mosaic of national providers. In the case of one famous company, they have 65 different relationships with national brokers buying separate products, it is a big headache for them, so it is not surprising most others opt-out.

Many who buy our product to their remote teams did not have a different health insurance before, simply because it broadly did not exist.

It is however my impression that people think it is fair that international remote team members get the same benefits as US based ones, and that when SafetyWing gets bigger, that will be obvious to everyone.

What tools does your company use to stay productive and in communication?

We use Slack for chat, Sococo and Google Suite for video and audio. We also have a very well developed and updated Notion for all company info.

On top of that we have also developed several internal tools and clever Slack channels that help a lot. For example a tool we call planning and prioritization, which is really just a Google Sheet for coming up with ideas and ranking them as a team based on impact and complexity.

How often does your company meet IRL?

Once per quarter, although probably less this year. Last three times we met in Mexico, Norway and San Francisco.

How do you track employee productivity?

We do not currently use third-party tools, although we have tried several. The reason is that they become too process-heavy and incurs little usage. We instead use a simplified version of a so-called OKR-system. That means we set yearly company goals (objectives), and then set measurable results on each of them. Every month we update on the progress, and people set personal quarterly goals to meet them. We look at these when setting our weekly goals, and this way it all hangs together.

We dont measure input any other way. We are very productive and as an organization we seem quite excellent at meeting our goals, so it seems that this sort of goal-driven system with high autonomy and responsibility on the individual works well.

Do you require your team to be online in specific time zones?

We do have so-called core-time meetings. This is 8-11am PST Monday, Wednesday and Thursday. The idea is that all meetings should ideally be placed in these time brackets. Tuesday and Friday are focus days. This works pretty well for people in Americas (morning) and Europe/Africa (afternoon) timezones, but is annoying for people in Asia. It is however the best compromise we have found to be able to coordinate using video, given that we dont want to go for a full async setup.

What do you think is the biggest mental transition from the office to remote work?

The biggest transition is self-management. People are so used to the bells and whistles of an office, that they often are not aware how incapable they are of managing themselves. Most people who start with remote, take some time to get through to healthy habits to take control of their workdays and use them the way they truly want to.

What advice would you give to a team just starting out as a remote company or a team transitioning to remote work?

The trick is to do the smart things bigger companies do, but from the start. Combine written and visual. Make a weekly check-in meeting where people update on what they did last week, and what they plan to do this week. Write celebrations regularly in #general. Have regular 1-1s. Make a yearly plan together, choose the most important metrics and create a dashboard everyone sees where it is updated by itself. Also set-up a regular session for brainstorming and planning for the future.

In regular companies you wouldn't do these things before you were bigger, because when you are small this is just the stuff you would naturally talk about. When remote, you need to do it from the start, intentionally.