0:00

Brett: All right, everybody. Welcome back to Founder Vision. Today I am speaking with Naman Mehrotra. He is the head of product at SafetyWing. Today I will be co hosted by Brian Gupton as well. He is our VP of sales. How is it going, Naman?Naman: Very good. Hey Brian. Hey Brett. It is nice to be here. I am excited to talk to both of you. Brett: You are joining us today from Venice, Italy. Naman: Yeah, Venice, Italy. It is a really nice day here. I am working from here for the rest of the week. Brett: Nice. We have got a nice spread of time zones between Italy, Colombia and Hawaii on this podcast, which is quite representative of both of our companies and what you guys do. My understanding is SafetyWing is creating options for health insurance for digital nomads and fully remote teams. This is something that’s actually very exciting to me because I’ve been looking for a real solution to this for over 15 years. I am really excited to hear about what you guys are doing. Naman: I think you got that right, Brett. I can start off and just give a very quick intro about Safety Wing. We are about a four-year-old startup that provides health care insurance and retirement products for remote workers worldwide. The way we see this is a replacement to national welfare systems. We envision a future economy on the Internet where physical borders are less and less relevant and people working remotely all around the world. We haven’t really seen these welfare systems or financial security and health care products adapt to that. We started with a digital nomad insurance product that first launched a worldwide health insurance product last year for global teams, and we have various other products in the pipelines, such as a retirement account and a few other financial security products. We are very excited about the space, and I think it has a lot of potential. We are basically just solving our own problem. Like you and like ClearView, we have a very global and remote team as well. Brett: Tell me about your experience coming into SafetyWing. How did you find yourself here? What’s your experience in being a digital nomad and working in this kind of environment? Naman: In terms of my experience as a nomad, I would say in today’s definition of being a digital nomad, I actually just started last month for the first time trying to be a full-time digital nomad. I left my apartment in New York City, and I have been in Europe for about a month now. I have plans of being in Europe for a little while, and then I am going to South America. It’s a pretty exciting time. I grew up in what would be called a nomadic family. My parents were moving countries and jobs every two to three years. There wasn’t a term called digital nomads then, so they were more kind of used to the expat terminology. We grew up across Europe, Asia, and Africa before I moved to the US for college and have been there for the last decade or so. In terms of how I found SafetyWing, I actually happened to stumble upon it. I had been a consultant in product at a consulting firm called McKinsey for a while out of New York, and I was just very excited about the startup world. I always knew I wanted to go out and start something or join at an early stage and build out a new product or team. I was just having conversations with a bunch of different people. I came across this company called SafetyWing, which is solving problems that were quite personal to me, because my family had been moving around. Every time we moved, we had to find a new health insurance carrier, new banks, and have a completely new life in every country. The company obviously was very, very interesting. It is a really global team, and I happen to have had a friend from college who had just joined three months before I did. After speaking to them, it seemed like a very natural fit, and I was very excited about the space as well. Brett: One thing that’s always occurred to me whenever I have thought of why this doesn’t seem to exist yet is the assumption is it must be so difficult to actually pull this off with so many different rules and regulations, and laws in all of these different countries. To really create both a health product as well as a retirement product and the whole suite of subproducts you might have related to that, to create something like that that really actually replaces what people are able to get locally but have it work across borders just seems like such a monumental, complex legal and regulatory task. How are you approaching that? Naman: That’s a really good question. The way we approached is kind of like every complex problem I think we typically approach. We broke it down into different steps and first started out with a product we thought would be simpler to accomplish. From the beginning of the company and when it was founded, there was a vision to provide health insurance and some of these kinds of retirement type products to freelancers around the world. But the reason we started the nomad insurance product, which is more like a travel insurance, is because we knew it would be much more seamless on the regulatory side to achieve and at least feasible to build something like that. That would give us enough resources and enough conviction in the idea that we can then go ahead and tackle the more difficult problems. We looked at it in a more incremental approach where we would have a pretty successful nomad or travel insurance type product. Then we started looking into the health insurance space, and even within the health insurance space, I would say a decent part of the world has less regulation around the health insurance space. I think the US and Canada particularly are very, very heavy on the regulation side. For that, we tend to take the approach of partnering with local entities, but where we can, we are building up to a perfect product. We start where we can with the best product we can, and over time we are building out and adding more and more countries to the list. Brett: Going back to the remote and distributed team’s thing, has SafetyWing been fully remote from the start?Naman: Yes, SafetyWing started off as a fully remote company. Brett: Being fully remote all along, you are in this parallel journey of working to solve a lot of the challenges of a fully remote team, fully distributed across a number of different countries and legal boundaries. You are also approaching and learning from all of the other lessons of being a fully distributed team, such as culture, maintaining interpersonal connections across the team. How have you been finding that as you have been working on this in parallel to spearheading solving some of these administration issues of being a remote team?Naman: To share some context, at this point, we probably have a total of 60 plus employees from maybe 40 plus countries. Time zone wise, I think we cover most of the world at this point. It has definitely been a very interesting journey. I will say one of the big advantages of being a completely distributed team is that a lot of our customers are distributed. We understand the problem, and we know that this is a real problem we are solving for ourselves and for a lot of our customers as well. That in a way brings us very close to our customers. We can even test products within the company and stress test them to understand if it is a real problem we are solving. I think for fully distributed teams as you both very well understand, it is a very different approach to how you keep the productivity up in the company and how you keep the culture strong and relationships between coworkers strong because you don’t see them every day. You can’t hang out with them outside of work or run into each other in the lobby. A few very specific things I have found to be very useful here is that we actually just had our first in person retreat since the pandemic started last year. In the weeks after that, I have noticed a big change. A lot of the coworkers met each other for the first time. I think with remote companies in general people tend to think that people never get to meet each other, but a lot of remote companies are actually doing in person offsites two or three times a year or sometimes even more. I think that’s essential to a lot of those companies. Some even have budgets for coworkers who work very closely with each other to go and meet each other and have a week of problem solving together and co-locate. I think those types of incentives or even policies are essential for remote companies to foster a very strong culture. I have also found one-on-ones, structured time to get to know a person outside of work, to be very important to build those deeper connections with my team. Brian: What about for entrepreneurs who are looking to either become a more distributed company or for people who are working at companies that are distributed? What’s some advice you could share about how to design your life around being a remote worker? For a product or engineering team, how do you develop a really good operating rhythm where things feel seamless, everyone feels included in those decision-making processes? Things can just operate a little more smoothly when people are working across multiple, different time zones. Naman: That’s a really good question, Brian. A few things I would say, on a high level, I am not sure if this is possible in a completely asynchronous way, but we have a culture at SafetyWing that’s semi asynchronous where we have a few meetings a week where everyone is expected to be online. I have found that works very well because there is some boundary around when everyone meets. A lot of the important issues we need to talk through happen in those conversations. That time is around 6 hours a week on a few different days. The rest of the work tends to happen asynchronously, and I have found compared to a company. I worked at a company that went remote, and a lot of the work was still happening in meetings. They were very time zone specific. At SafetyWing, I think things are more optimized for offline work. We use Notion. We use Slack very well to get work done offline and really push things forward without having to have meetings. In terms of some very unique things we do, for example, a lot of us in our Slack status have the country and the time zones we work out of. There are these cultural norms we have created for distributed teams that make it fairly easy for you to at least know how the other person’s working style is and adapt to that. Over time, once you are working very closely with your team, you tend to understand their working hours, the way they work, whether they like meetings or not and really adapt to that. I would say those are really, really important. I have found a lot more opportunities to get deep work done with remote work because there is no expectation of being online for meetings at all times. You can design your day around when you are most productive. Really understanding that about your teammates is I think very, very important. Brian: Have you found there are certain roles in the organization that are just more challenging to work in an asynchronous fashion? Do you think it is just a matter of figuring out the operating rhythm that’s going to work? I would think customer support would be a tough one to work asynchronously. If I have got a support issue and the person that needs to work on that support issue is fast asleep and they are not going to see the issue for eight to 10 hours, how do you handle positions like that where the role in and of itself is a little more challenging to do asynchronously?Naman: You hit the nail on the head with that. I would say more operational roles that require someone to be online 24/7. For us, for our relationships with companies, for example, account management or customer service, these types of roles, definitely as a company, you want to be online 24/7. The way we have structured it is we have people across the world that handle different time zones. If we are partnering with a partner from a particular time zone or a particular region, we have account managers or customer service targeted towards that region. That’s how we have dealt with it. With other roles, with engineering, the engineering org, the product org, we haven’t really had any issues with roles that need to be co-located. I have found with some sort of problem-solving exercises, it does help to be in person. Sometimes I think it is beneficial if I am working with a particular engineering team on starting a new product or building out the vision for a new product. I do find it helpful to co-locate with them for that part of the process. Brian: I guess it is simple enough now with the tools we have to virtually co-locate. It almost makes it easier if you need to pull together a small team to tackle a specific issue, you can just pull from anywhere in the world. You guys just agree on a time when it works for everyone to get together. From that standpoint, things have gotten quite a bit easier. Your tool is obviously some of the operational challenges for just being a remote worker, but I know you specifically are focused at SafetyWing on APIs for the development there. How do you guys look at that as a way to easily enable some of this complexity in the various regulatory environments?Naman: The API is a new part of SafetyWing. What we found was there are a lot of businesses and platforms across the world that are offering services to other businesses or small to medium sized companies that don’t want to deal with the logistical hurdles of starting a remote company. If you hire someone from a different country, they need a different payroll structure, tax structure, and benefits. There are a lot of these companies. One of our partners, like remote.com, deals with a lot of the people and logistical hurdles. What we have found is that they also want to provide benefits to their customers. If you have looked at the trends in the fintech space, APIs have become a very, very simple way of providing infrastructure today. The way I analogize it is if you look at electricity, APIs are sort of the power socket that enables all the other applications that come with it, like a toaster or microwave oven. We look at benefits the same way where they are essentially infrastructure everyone should be able to have access to. We are building this API so a new platform or a new company that’s starting, if they want to integrate global benefits onto their platform and provide them to their customers, it is really easy for them to do that. They don’t have to think much about the logistics. That’s our future vision with the SafetyWing API. Brett: For onboarding for new clients, let’s say there are companies who have been fully co-located and over the course of COVID, they have started to become more remote. They have already got a large team with localized benefits. Then they start having this distributed team, and they are starting to bring more people in from overseas. They have got an existing legacy benefit system, and then they have a growing population of new employees that would benefit from something like SafetyWing. How do you approach that interface with these new customers and help them have a seamless experience for their employees to be able to select what kind of benefits they have? Then also have some form of parity across the organization. Naman: A lot of our customers, because we launched this product last year, in 2020, we have been working with a lot of new customers that haven’t had to transition from a co-located insurance model where they have a significant number of employees in a particular country to a completely distributed one. In many of those cases, it is actually a very incremental transition. For example, we have worked with companies where if they have a significant number of employees in a particular county, Mexico or something, and because of this remote work, they are now starting to hire people abroad, they will approach us for that specific use case. They will keep those Mexican employees on the same insurance because that’s all set up and a lot of times it is cheaper than a global insurance plan, especially in developing companies. Then, they will start off with a more global plan for the rest of the world. We have seen a lot of those types of customers. Over time, we are also hoping to offer a product that’s specific to developing countries where you need a much lower cap product, and you don’t really have requirements like in a lot of North American, Europe where healthcare is much more expensive. That we hope will be a lot more competitive with a local health insurance provider and can cover that use case for them as well. The real value in SafetyWing right now for a lot of these companies is that for every new country they go to, they don’t have to get their own local insurance plans, which is a pain to deal with. It only makes sense for them to look at local insurance plans if they have a huge majority of people in a particular country, and then for the rest of the world they come to us. Brian: When you are building a team, what are some of the characteristics you look for if that team is going to be fully distributed? What is some advice you can give to people to be a more effective leader of distributed teams?Naman: I think one very important characteristic I have found is the autonomy that someone is used to before. We find that a lot of distributed teams we work with generally tend to be a lot flatter than your typical co-located organization. People are used to a lot more autonomous work. I almost look at it as a lot of individual contributors that are owning very significant parts of the company. People who have done a lot of that type of work before and taking ownership of bigger work streams and like working in that manner rather than a more prescribed way of working, I think tend to do a lot better in remote teams, especially because you don’t have a lot of optics involved in a typical office style environment. Autonomy I say is really, really important. I think I would say this is a potential con of remote work, which is for people fresh out of college or fresh grads, I have found that training and onboarding can be very difficult early on in your career. A more experienced individual who has done something for a few years finds it a lot easier to transition to remote work and know how to do things. I found this at McKinsey as well. A lot of fresh grads we were hiring who were coming into McKinsey completely remote, they just didn’t have a lot of the training, resources or coaching that you get one-on-one. That I have found to be lacking in most companies today that are remote. I think one important thing to do as a leader to try to solve those issues is to have more structure around coaching and understanding development goals of the team. That could be something like having very structured conversations around development goals, not only work focused but even personal focused, and see how you as a company or you as a leader could help them and give them more opportunities to develop those. Having regular one-on-ones or conversations around that I have found is very, very helpful. Two, I would say, is being very, very clear about the cultural values of the company. I think our founders at SafetyWing have spent a lot of time thinking about what kind of culture we want to build and what the important norms and values are that drive us. It is a big part of the onboarding process and even the hiring process where we will take a lot of time to get to know someone and understand if their values align with the company. In some situations, it inhibits the company from hiring quickly. We would say the long-term benefits of getting someone who is aligned with the culture, especially in a remote team, is very, very important. We spend a lot of time and effort putting those values together and making sure they are aligned with a new hire. Brian: What are some of the things you would consider a non-negotiable when managing people who are mostly working autonomously? For us, since we are not doing a regular standup each day, we will post these on Slack and that’s one of our non-negotiables. You need to update everyone on what you are working on that day. I’m thinking practical things like that, or if you want to take it in a different direction. I am interested to hear. Naman: I think one is we have regular weekly meetings, Monday meetings, where we expect everyone to be very present, active and talk about any big blockers. That’s where our semi asynchronous culture comes in. I think being present there and talking about what has happened in the past, what will be done next, and sharing updates there is very, very important. Being responsive on Slack within a one-day period if that person is not offline is another important thing. Then just taking direct ownership of a workstream and pushing that forward is another non-negotiable, which comes back to our conversation on autonomy. I would say those are typically some of the most important things I see. If they are stuck on something, instead of just waiting around or not talking about that blocker, we really prefer that those are brought up early on so that the team can problem solve before we move on to things. Brett: Before we close, I have one note from your pre-call with Brian that I really want to dig into a little bit and hear your story here. Apparently you were in Egypt for the revolution. Was it the Arab Spring?Naman: Yeah, that’s correct. It was in 2011. Brett: Tell me how that was for you. What was your experience with that?Naman: I was actually in high school then. I had just moved to Egypt about a year before it happened. My experience in Egypt before that was as a foreigner I was kind of in this bubble, and I thought it was very safe and having that rosy picture of Egypt. Then with the Arab Spring, it was January 26, 2011, I think. It started off as something that seemed much smaller and grew into something really, really large. There was a million-person march in Cairo. My high school was obviously cancelled, and the company that my dad used to work for was told that my family could be evacuated in a matter of a few hours. We had to really pack up all of our belongings and be ready for that. As a kid, I don’t think I completely understood the gravity of the situation, but it did shape my life in many ways. For that weekend, things kind of got really bad in Cairo. There were a lot of protests. The police weren’t available to stop a lot of the robberies and things like that that were happening in Cairo. Then when the coup was announced, our company decided to evacuate us to Italy. I spent three or four months studying in Italy, which was actually my first time living in a developed country. That was a pretty defining moment for me and made me want to work more in technology because I thought about the causes of the Egyptian revolution. I think it would be very difficult for something like this to happen if social media didn’t exist. A lot of the success of the Tunisian part of the Arab Spring spread over to Egypt, and that’s why there was this kind of organized protest. In order to prevent people from being organized, the government had shut down all cellular services. I remember that. The only thing that was working was landline.That was a very, very obvious picture of how technology can do good in the world and get people together to follow behind a cause. Brett: Fascinating. Thank you so much for joining us, Naman. I am really excited to continue talking with you more offline about SafetyWing. This is a problem I’ve been looking to find some solution for for us for a very long time. I am really excited about how we can help you succeed in this vision and bring this to the world. Naman: Thanks a lot, Brett. I really enjoyed speaking with both of you as well. I am excited to keep working with both of you. Brett: Thank you all for listening to Founder Vision. If you enjoyed today’s episode, please subscribe and share it with your friends. I am also really grateful for your five-star ratings and reviews as well as any feedback about what we are doing well and how we can make the podcast even better. To send feedback or connect us with a potential guest, reach out to [email protected].