Sasha Gainullin - CEO of battleface and Robin Assist: Creating a 24/7 Company, Pivoting the GTM Motion, and Balancing Accountability and Autonomy

Sasha Gainullin  00:00

On October 7, a terrorist attack in Israel happened, leaving 4,000 travelers stuck in Israel, 3,000 travelers trying to get to Israel, and 2,000 potential travelers who were still at home planning to travel to Israel. All of those customers were calling in for help from all different directions. If we had a company filled with people who didn't know how to answer a call, respond to an email, or assist a customer, we would have failed miserably.

Callan Harrington  00:37

You're listening to That Worked, a show that breaks down the careers of top founders and executives, pulling out those key items that led to their success. I'm your host, Callan Harrington, founder of Flashgrowth, and I couldn't be more excited that you're here. Welcome back, everyone, to another episode of That Worked. This week, I'm joined by Sasha Gainullin. Sasha is the CEO of battleface and Robin Assist. battleface is a global company enabling customers and partners to easily select travel insurance products and services that perfectly fit their needs. Robin Assist is a tech-driven emergency travel assistance platform supporting the travel insurance industry.  Prior to battleface and Robin Assist, Sasha was the interim CEO of Tangiers Group, and before that, he was the COO of Tangiers International, both of which were deep in the travel insurance space. Sasha has a really interesting story, and I loved diving into it. We talked about the power of immersing yourself in an industry. To say that Sasha is an expert in the travel insurance space would be a gigantic understatement. We also dove into how Sasha built a 24/7 international company. This is an area where I have very limited experience, and one of the things I didn’t realize was some of the unique challenges that come with building a 24/7 international company. A big one that I hadn’t thought about was how to balance autonomy and accountability because you've got different time zones, and people are working at different hours. I loved hearing how Sasha navigated this. The part of the conversation that I loved the most was talking through the pivots that Sasha and his team went through when building Battleface and Robin Assist. They took on some wild swings and came out much stronger as a result. I think it's a great listen for anyone who’s either part of or building a hyper-growth company. So with that, let’s get to the show. Sasha, I’m excited for a number of reasons, obviously. You started an insurance company in a unique area, so I've got a million questions on that. But to kick this off, I wanted to hear about the transition from moving from Russia to Wisconsin.

Sasha Gainullin  03:12

I was pretty young, about 15 at the time, just turning 16, and I was an exchange student. I had the chance to study abroad for a year, so I went to high school in Stevens Point, Wisconsin. In Russia, we only have 11 grades, and here in the States, it’s 12, so I essentially came for the last year of high school, and I guess I never exchanged back. I was supposed to be here for a year. 

Callan Harrington  03:37

Did you know—I'm going to ask some dumb questions here—did you know a ton of English when you moved here?

Sasha Gainullin  03:44

Not necessarily. I was studying German in Russia, and I started taking English classes, but it was just the basics—alphabet and maybe just a few words here and there. For me, the most incredible experience was living with an American family and being immersed in the culture right then and there. I've met so many immigrants who moved to New York or California and were part of a Russian community, speaking Russian, but I moved to the Midwest, to the heart of America—to Wisconsin. Weather-wise, it was a perfect match with Russia, but everything else was definitely a new experience.

Callan Harrington  04:29

When doing research on this, I found that The Golden Girls had a big impact on your language skills. Can you walk us through that?

Sasha Gainullin  04:37

So my host mom had this fascination with different sitcoms and soap operas. The Golden Girls was one of them, and she was actually recording them. She had massive tapes, not just of that show but also Guiding Light, I Love Lucy, you know, the classic sitcoms and soap operas. But The Golden Girls were just funny to me. The language was simple—the terminology, the jokes. At some point, my language started to sound like theirs. I remember for the longest time I would say, "Well, give me the benefit of the doubt," directly from Guiding Light, without really knowing what it meant.

Callan Harrington  05:19

That’s amazing. My girlfriend has been caregiving for her grandparents for the past couple of years, so there’s been a lot of Golden Girls watched, and I’m shocked at how well it holds up today. 

Sasha Gainullin  05:36

My kids, who are 8 and 12, love it. They’re entertained by the way they dress, the way they carry themselves. I didn’t seek out friends who liked The Golden Girls, but it happened to be that all my best friends know and like the show. We always joke about retiring together like them toward the end. It’s a cool show.

Callan Harrington  05:57

I love it. Switching gears, you’ve got a travel insurance company now, and I’m super curious to dive into that. You’ve got a long legacy in the travel insurance space. Where did this all begin?

Sasha Gainullin  06:13

Back in Stevens Point, Wisconsin, so it's a small town, but it happens to be the mega center of travel insurance, simply because of one guy, John Noel, who's essentially like the warren buffet of travel insurance. He started a company in his basement called Travel Guard, which is now a massive global travel insurance operation that was owned for the longest time by AIG and most recently, was purchased by Zurich when I was in Stevens Point. John was looking for as many people as possible to join the company that either traveled or were coming from another country or spoke another language, and I had an opportunity to join the company in exchange for getting a scholarship to go to University of Wisconsin back in the late 90s, the entire world was different. It was pre technology, and everything was done over telephone. But that gave me a massive boost into really understanding what customers are looking for without looking at them. Back in the late '90s, the world was different. It was pre-technology, and everything was done over the telephone. But that gave me a massive boost into really understanding what customers are looking for without seeing them.

Callan Harrington  07:16

How many times, when you got into a claims dispute, did you say, "Give me the benefit of the doubt?"

Sasha Gainullin  07:22

Yeah, exactly. I used quite a bit of that language. They didn’t know I had been primed for this.

Callan Harrington  07:32

Here’s something I’m curious about. You went up to the executive level, all the way up to CEO, at companies that were the epicenter of the travel insurance space. Was this something where you really had a passion for the travel insurance problem, or did you build such a unique skill set that you kept getting the next good opportunity? For me, I spent a long time in insurance myself. I don’t know that I’ve got this overwhelming passion for insurance. I do have a lot of passion for the small business owner and the agency, but I found I just started gaining this unique skill set that happened to be in demand because insurance companies are large. What was that like for you?

Sasha Gainullin  08:22

I think it was luck. I had the chance to work alongside an amazing entrepreneur who was extremely open-minded and gave me, and a few of my friends, many opportunities. Many of those friends are now also part of battleface. We were 19, 20 at the time, and the company was growing so fast. We got a contract with American Express to provide 24/7 emergency travel and medical assistance services to all of their card members. That was the first major contract that changed the trajectory of the company. We didn’t have a plan for it—we were just figuring it out as we went. The executive team of Travel Guard was incredibly flexible. They gave us the opportunity to say, "Here’s a problem. How can you solve it?" I was very interested in the problems we were solving because we were helping people who were traveling globally. They were looking for emergency cash, wires, medical help, making travel arrangements, or finding lost luggage, and I just found it fascinating.

Callan Harrington  09:27

You love this problem, is that what I’m hearing? The question I’m curious about is, since you were rising up the ranks and had good executive positions all the way up to CEO, why start a business at all?

Sasha Gainullin  09:45

There were multiple reasons. What we started to see in the industry was that the travel insurance product never changed. It remained the same from the late '90s. Whether you travel from Columbus to New York or Columbus to Nairobi, Kenya, it’s the exact same product. These products became overly commoditized and filled with benefits that, in the end, didn’t work for travelers. We started to see a lot of cases where we couldn’t help customers because their policies weren’t working for them. We wanted to solve that problem. How can you create a platform or a company that can create products for your specific trip?

Callan Harrington  10:31

You wanted to be part of the solution, but you couldn’t be part of the solution where you were at—is that right?

Sasha Gainullin  10:36

The industry became very hard to make changes in. From the early days, when we first started out, we could establish operations and were empowered to make decisions quickly. We saw an opportunity to create a unified platform—a single global company that could help people from buying the policy to getting the services behind the policy.

Callan Harrington  10:59

What was the spark where you thought, "I have to actually do this?" You had to raise capital for this too. What was the spark that made you do it? 

Sasha Gainullin  11:09

At the time, I was based in Malta, Europe. We were working on developing underground emergency response services on behalf of big insurance companies in hard-to-reach places across the Middle East, Africa, and Asia. We were developing claims and medical networks and helping people who were either working in these places or were expatriates in these countries. What happened was that we started to see a lot of travelers in these countries without any insurance—journalists, contractors, NGO workers—simply because they couldn’t find a policy that would cover that specific destination. Because of our relationships with insurance companies, we went to Lloyd’s of London, sat down, and started to dissect the problem. How could we change that? Why is it that this particular traveler cannot buy insurance? The answer was pretty simple. The idea came from Lloyd’s directly: If you can figure out a tech platform that can price out risks in real time, based on destination, based on where the traveler is coming from, and then dynamically build their policy, we will support you all day long because that’s one of the biggest problems that insurance companies are having—there was no platform out there that could price these risks.

Callan Harrington  12:29

I have to assume—and correct me if I’m wrong—but could you start this business without having a background similar to what you had? You can’t just walk into Lloyd’s in London and say... How critical was that experience?

Sasha Gainullin  12:42

It’s so critical. You have to come from this background and experience. You have to know travel insurance. Let’s say you’re traveling in Argentina and you’re going to a hospital. There’s no guarantee that the hospital will say, "Yes, this is a credible insurance policy, and we’ll treat you." The undertaking is massive, but once you live and work within the space, you know how to maneuver all of these angles.

Callan Harrington  13:07

For our listeners who may be unfamiliar, Lloyd’s of London damn near invented insurance. A lot of people may be familiar with Lloyd’s of London because they’ll insure an athlete’s arms or whatever, but Lloyd’s of London also handles all sorts of unique risks. It’s a gigantic company. So it’s not just that you had to convince investors that this was a good idea—that’s just a piece of it. You actually have to work with someone who’s going to underwrite this and back you on that, which is probably even harder than just the capital side. Would you agree with that?

Sasha Gainullin  13:39

Yes, 100%. You’re dealing with companies that have been around for centuries, so they know the risks, they know what you’re putting together, and they can see if it’s going to be the right product or service. But also, because they’re putting a 100% guarantee behind the products in the event of a claim, it’s Lloyd’s of London at the end of the day that would be paying the claim, not you, Sasha, with battleface. That’s unrealistic. They also have to have 100% trust in you to deliver the product in the right way, compliantly, and essentially speak on their behalf with consumers. Before you even go out to the VC market and raise money, you need to convince insurance companies to actually back your products.

Callan Harrington  14:28

Talk about a huge stamp of approval when you go in there with that. It’s a different conversation because you’ve got pretty solid validation. You still have to execute, of course, and that’s one of the interesting things about insurance. It’s not just about "sell, sell," because if you sell and you didn’t price that product right, you’re out of business. There’s nothing that you can do. So one of the things I’m super curious about is in doing research on this and hearing some of the other talks you’ve given, you mentioned a lot about how when someone typically gets a travel insurance policy, there are so many restrictions that it hardly ever pays out. People get frustrated with it, and you wanted to come in and change that. My question is, from a go-to-market perspective, where did you start? How did you start getting clients? How do you change how consumers think about a product that they’ve known to be one way for eternity?

Sasha Gainullin  15:28

It’s a complex question because it depends on the country. In the U.S., we don’t think of travel insurance as a necessity when we travel, whereas in Europe or the U.K., that’s where we started. British travelers travel with travel insurance—86% of them. In America, before COVID, only 23% of Americans bought travel insurance. But in the European markets, where travel insurance is at the top of everyone’s mind, it’s the actual value proposition. For us, in travel insurance in general, you can’t scale without partnerships. Direct-to-consumer models in travel insurance don’t really work. Travel insurance is best sold as an embedded product while you’re booking your trip, for example, with an airline or online travel agency, or as an embedded product as part of your credit card or memberships and associations. The channels are absolutely vast if you have a customizable product for each of these channels.

Callan Harrington  16:32

I’m super curious about this because the association route can be a great route, but one of the biggest challenges companies have is they can sign the deal with the association, but now you actually have to get the members to buy the product. How did you drive adoption?

Sasha Gainullin  16:49

Well, it was very challenging. We didn’t, actually. It was pretty flat. We had to rethink our model because I remember signing this massive association deal with millions of members, but nobody bought a single policy. So we went back and started looking into how else we could maneuver and what we could do to help the association. We started working on creating different membership tiers where you can at least start embedding some of the benefits into the membership, making it more valuable. But again, it sounds like we cracked the code, but we didn’t. It wasn’t anything to be proud of. It just gave us an ability to test, and we continued to concentrate on the technology aspect of it and how we could continue to redefine the product and services. But nothing was really working.

Callan Harrington  17:47

So it sounds like COVID-19 was the catalyst. Is that fair?

Sasha Gainullin  17:50

COVID-19 brought massive scalability. 

Callan Harrington  17:54

What was the moment?

Sasha Gainullin  17:56

When COVID-19 happened, the number two exclusion in most policies is pandemics. That immediately eliminated over 90% of travel insurance players in the world. They either stopped selling travel insurance or stopped being involved in travel insurance altogether. But we continued to sell, offering the product while adjusting our pricing based on the risk with Lloyd’s and based on destination. People were still traveling, often for family emergencies, or because of different lists of where you could and couldn’t travel, which kept changing. The moment came when a journalist tweeted somewhere on social media, “You should check these guys out; they’re still selling insurance.” And then it just started to grow from there. It was very organic. I remember these massive social media groups, like "Liverpool Residents Traveling to Majorca, Spain," where suddenly hundreds of people were talking about battleface being the option for travel insurance, or German travelers going to Italy. That’s how it started to grow—extremely organically. I remember our phone lines blowing up overnight. We didn’t even have the right telephone system. We had to upgrade our phone systems and everything else because suddenly it was just madness—24/7 sales through the roof. People loved it because it was easy to purchase and very fast, but then our biggest obstacle was, "Why is it that the entire world isn’t selling travel insurance, but you are?" This is where Lloyd’s backing really helped. We could say, “Look, we’re legitimate. Lloyd’s of London is underwriting our insurance policies.” Because many customers didn’t believe we were a real company, especially with a name like battleface.

Callan Harrington  20:04

I mean, that makes complete sense to me, right? If nobody else is doing this, how are you able to do it, and is this actually going to pay? How did you face that challenge? Of course, you had Lloyd’s of London, but did you have to start social proof-type campaigns, where claims were paid, or did you promote that? What did that look like?

Sasha Gainullin  20:26

I remember immediately opening a Trustpilot account. It’s very popular in Europe and starting to gain popularity here as well. It’s an independent review channel, and we started attaching that to our website and putting it at the forefront, asking customers to rate and leave reviews. That took off quite nicely, and it was all four to five stars immediately. But because we were solving journalists’ issues at first and creating products for them to travel to certain places, journalists were talking about us as a company. I remember a friend of mine in London calling me and saying, “Holy shit, BBC is talking about you!” That helped us a lot as well. So our very first customers were spreading the word about us.

Callan Harrington  21:11

Because of the virality of this—these were big groups—people started to realize what you did. You started to evangelize this. And of course, I have to assume at this point you were hiring a lot of people to help support this demand. Is that right?

Sasha Gainullin  21:24

Not necessarily, because we were pretty cheap, you know. We’re still pre-Series A. How we were able to scale was by pulling our friends from the industry to come and join us, but in different time zones—in Europe, the U.S., and Australia. We started to build the company like that, so we didn’t have to have a massive 24/7 call center in a single location. COVID was a devastation for the world, but we were learning as we went how to create a scalable, remote company infrastructure. We focused on the most critical points: how to build a 24/7 company utilizing different time zones.

Callan Harrington  22:13

How do you make that work? I’m just curious, like getting into the weeds here—what’s the cadence like? How do you make sure people are included? What does that look like?

Sasha Gainullin  22:24

There’s no magic formula at all, and of course, there are lots of opinions out there, but they’re all unique to their situation. In our specific world, what we learned is that we have to bring in people with experience. We have to bring in people from within this industry or who come from industries where they’re very passionate about helping people—that’s number one. Number two is autonomy—really allowing everybody in the company to create, be responsible for their creation, and drive that creation forward. And number three is being able to communicate with each other, work through different problems, and achieve results. Those are the three core areas that I usually concentrate on.

Callan Harrington  23:09

How do you balance autonomy and accountability?

Sasha Gainullin  23:13

Measurement by results, of course. Communication, being upfront, and being open to feedback. The autonomy is there, but we’re still challenging each other, still talking to each other. I personally never make a decision alone. I always have to have someone’s feedback and communication, regardless of how small or big the decision is. That probably comes from my background in emergency travel and medical assistance. If you’re working with someone in a remote area of Kenya, in a hospital, and you need to help that person and their family get back to the United States, you can’t possibly handle that on your own. You have to be working as part of a team.

Callan Harrington  24:03

You hit this moment of extreme growth. Did that continue, or did you hit a wall at some point and have to move around it? What did that look like?

Sasha Gainullin  24:15

No, it didn’t continue. It stopped. Well, it didn’t stop at 0%, but we thought, "This is it. We’re going to take over the travel insurance market as a direct-to-consumer brand. This is our destiny. It’s working, and it’s growing massively." One of the mistakes we made was not realizing that it was just the COVID-19 era. Once COVID-19 was over, everybody else was back with massive distribution channels, partnerships, and brand names. So the direct-to-consumer strategy, post-Series A, was our plan to grow the company and become the travel insurance company for customers to choose from. But it became extremely expensive. Organic channels were working, but not at the scale we needed them to. Paid channels were impossible to afford.

Callan Harrington  25:15

Insurance is so high in general—any insurance.

Sasha Gainullin  25:18

It’s just bizarre. When you start diving into the actual economics, it just doesn’t make sense. Post-Series A, you have this expectation—you raise the money, you start hiring a lot of people. But then what we needed to do was quickly pivot back to the B2B model and away from direct-to-consumer—not completely away, but we just couldn’t concentrate on it so heavily. We had to go back to our value proposition. What makes us so special compared to the hundreds of other companies out there? That’s when we started diving into what customers loved about us and how they were responding. These were the exact same customers going to airlines, online travel agencies, or credit cards. We just invested a lot into tech infrastructure that essentially pulled apart travel insurance into every individual benefit. There are over 50 benefits, for example—a single benefit to insure your luggage, a single benefit to insure your flight, a single benefit to insure your inconvenience if your flight is delayed for more than three hours. We concentrated on each benefit and the channels that benefit would apply to.

Callan Harrington  26:43

You went through these partnerships the first time, but they didn’t work. You had explosive growth going direct-to-consumer, but that slowed down. You needed to pivot again. Was it the fact that you could say, "Here’s who our ideal customers are," and show this to partners to get them to move, or what made the partnerships successful this time around?

Sasha Gainullin  27:06

Conversion rates. Post-COVID, consumers are a lot more educated about travel insurance. Before COVID, maybe 23% of Americans were buying travel insurance. That number is now 52%. Any type of global disaster—whether it’s September 11, the tsunami in Thailand, or a volcano eruption—elevates the knowledge and importance of travel insurance. Brands are looking for products that actually work for their customers because we started to see a lot of major travel distribution partners whose conversion rates were dropping because their customers were saying, "No thanks," to travel insurance. That’s what we’re proud of—the conversation within the industry shifted from "How much can we earn upfront from selling an ancillary revenue product like travel insurance?" to "How can we concentrate on conversion rates and deliver relevant products for our customers?" and "How can we create products that are unique to our marketplace?"

Callan Harrington  28:23

Customizing the offering to what those customers of those partners specifically are demanding. 

Sasha Gainullin  28:28

That’s right. A lot of players in the travel industry quickly identified that, as unique as their company is, their ancillary revenue products are exactly the same when it comes to travel insurance as their competitors’. They wanted to know how to actually change that.

Callan Harrington  28:45

What has to come next for battleface to hit that next level?

Sasha Gainullin  28:52

We have this global company that we’ve built, and we’re growing through partnerships. I think we’re reaching the point where 90% of our revenue is generated by B2B partnerships. But there’s one element in the travel insurance industry that is so annoying—the actual services. There are so many parties involved in the chain, and they’re all very disparate, not talking to each other because they’re not technologically connected. That was a problem we were solving for ourselves. We wanted to ensure the customer had the exact same experience. While creating unique travel insurance products outside of Lloyd’s, we’ve developed nearly 10 to 12 insurance company relationships that are backing our products in Australia, Canada, and throughout Latin America. We have this massive network of insurance carriers that, outside of our products, are also selling their own products in the travel insurance space.

Callan Harrington  29:51

So this is a true B2B play. The partnerships are B2B2C, and then this is a true "we’re selling to other travel insurance companies."

Sasha Gainullin  29:59

That’s right.

Callan Harrington  30:00

One of the questions I love asking founders who have hit this scale—you’ve got over 100 employees on LinkedIn, you were the founder, and you’re still the CEO—how do you make sure you’re keeping your skill set up to the level to still be the right CEO for the job?

Sasha Gainullin  30:18

Well, everyone probably has a different answer. For me, specifically and personally, if I can still pick up the phone, talk to a customer, and give them the answer—whether they’re buying the policy, filing a claim, or needing help—then I’m still current. If I’m just sitting in a boardroom or somewhere, and I have no clue and am just looking at the performance of the company based on numbers, then it’s a massive disconnect. This is where I think innovation stops. Then you’re just becoming a bureaucratic company. At least in our industry, you have to have a direct connection to the customer and your employees. There are a lot of challenges that we see every day. In our industry, those challenges could be internal or external. For example, last year, when we onboarded a massive partner on the B2B side of our business on October 1, 2023—a huge accomplishment for us—just six days later, on October 7, the terrorist attack in Israel happened. We had 4,000 travelers stuck in Israel, 3,000 travelers trying to get to Israel, and 2,000 potential travelers who were planning to travel to Israel. All of those customers were calling in for help from all different directions. If we had a company filled with people who didn’t know how to answer a call, respond to an email, or assist a customer, we would have failed miserably. But we were able to attend to every single request that came in flawlessly. 

Callan Harrington  32:07

Does the company have to be able to maintain what you just described, where the CEO can still pick up a call? Or do you think at some point it’s just going to have to be bureaucratic, and you’re just not interested in being there at that point?

Sasha Gainullin  32:22

You have to be able to make decisions right then and there. It starts with everybody in the company. It doesn’t matter if you’re the CEO, working in the call center, or in the claims department—you have to have the ability to solve problems in real time.

Callan Harrington  32:37

Sasha, last question I have for you—if you could have a conversation with your younger self, what advice would you give? What would that conversation be?

Sasha Gainullin  32:45

I’d probably have a whole list of things to tell myself not to do or to do differently. I know I’m supposed to say I have no regrets or whatever, but I’m definitely not that person. There are a lot of mistakes that I’ve made, but in the end, it all worked out, and it was absolutely fine. But in general, I think things work out. If you think about a problem and ask yourself, "Three years from now, is this actually going to be important?" The answer is probably not, so there’s no need to worry about it. I was lucky to have a lot of people around me to tell me those things, so I was always pretty calm about anything that happened.

Callan Harrington  33:30

Isn’t it amazing, though, when you look back at some of those early business challenges that felt like, "Alright, this is it. This is the one that’s going to tank it," and then you look back and realize, "Oh, that wasn’t even close?"

Sasha Gainullin  33:41

Yeah, I do actually remember half of them, you know. Most of the time, things work out. What really helps is talking through all of this with your friends, colleagues, and mentors, and really getting that feedback. I was lucky throughout my life to have people around me who listened. Maybe it’s The Golden Girls.

Callan Harrington  34:06

It’s The Golden Girls, yes, hands down. It’s come full circle—the cheesecake.

Sasha Gainullin  34:11

Yeah, in the kitchen.

Callan Harrington  34:14

Sasha, this was a ton of fun. Thank you for coming on.

Sasha Gainullin  34:17

I really appreciate it. No, this was fun. Thank you.

Callan Harrington  34:24

I hope you enjoyed my conversation with Sasha. I loved hearing how Sasha built such an adaptable company. If you want to learn more about Sasha, you can find him on LinkedIn in the show notes. Also, if you liked this episode, you can find me on LinkedIn to let me know. And if you really want to support the show, a review on Apple Podcasts or Spotify is very much appreciated. Thanks for listening, everybody, and I'll see you next week.