Marketing Borderless Insurance For Distributed Global Teams Today | Joey Flores from SafetyWing

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Stay relevant to your visitors and increase conversions by 50% by adding Pathmonk to your website in seconds. By letting the AI do all the work and increase conversions while you keep doing marketing as usual, check us out on Pathmonk.com. Hey everybody. Welcome to today’s episode of Pathmonk Presents.

Today we’re joined by Joey Flores. He’s a former YC founder. He is the head of marketing at SafetyWing. Joey, I’m glad to have you. Welcome to the show.

Joey Flores: Thank you, Rick. Good to be here.

Rick: Amazing, Joey. Let’s get right into it. Let’s not waste any time. Let’s start with the basics. Maybe what’s the big idea behind SafetyWing and if you were to explain it to a friend over coffee, how would you describe what you do?

Joey Flores: I would basically talk about the fact that, increasingly people are living borderless lives. They’re going all over the world. Airfare travel has dropped to very affordable rates, which allow people to travel quite a lot.

I myself have been fairly nomadic for almost nine years, during which time I’ve spent time in about 18 different countries. And SafetyWing’s founders realized that there’s a bit of a problem with a lot of the social safety nets that people are used to—whether that’s health insurance or income protection, disability and things like that—which are oftentimes provided by the governments of our countries and our states, and tend to break down when you are traveling and living a more global life.

When you’re not in your home country, you have a hard time accessing healthcare and things like that. So SafetyWing builds products to unlock your global aspirations and allow you to move about the world freely.

So we have health insurance, we have travel insurance, we have life insurance and other products that are borderless. They work in over 175 countries. There’s no specific network that you need to go to. You can go to a hospital in some rural part of China and then file a claim against the policy from anywhere you’ve been treated.

Rick: All right. That’s impressive. Would you say—trying to understand your ICP a little bit more for context—is this for the travel nomad, the commuter that travels a lot, or is it for everyone? Is there a specific persona that you’re targeting?

Joey Flores: Yeah, so we have two divisions of the company. We have the B2B side where we provide healthcare plans for companies. And what makes our product unique is that it does work all over the world.

So a lot of times these days, companies have a few employees in Colombia, a few in Israel, a few in the United States, a few in Australia. And rather than having to get an Australian plan and a Colombian plan and a different plan for every teammate, you can get the SafetyWing plan and cover all of your employees around the globe with one plan.

So that’s one of our ICPs: distributed teams, oftentimes with a presence in three or more countries.

And then on the consumer side, we really focus on long-term travelers—expats, long-term travelers, families living abroad, et cetera. Certainly you can pick up our Nomad Essentials product and hold onto it for one or two months while you’re taking a short trip, but we really build these with the long-term traveler in mind—people who spend probably half or more of their time every year not in their home country.

Rick: Makes sense. And it’s more and more common these days. How do these people discover you? Simple Google search? And what are your go-to marketing channels for bringing in more of those people?

Joey Flores: We have a super robust ambassador program. So we work with a ton of influencers and creators on YouTube, TikTok, a lot of bloggers and people like that.

So to some extent, we really let other people tell the story of SafetyWing. We have a lot of travel creators who use our product, who are loyal customers, who have had tough situations happen while they’re traveling and SafetyWing has been there for them. So a lot of our promotion is through this ambassador program—working with creators and ambassadors.

Rick: How much of a role does your website play for bringing in new business? Anything that you think works well for conversions right now, or anything you’re focused on improving?

Joey Flores: Our insurance is not really an impulse buy, so oftentimes we need multiple touchpoints. People hear about us a couple of different times before they actually pull the trigger.

Sometimes they’re planning a trip but they’re not leaving for three or four months. We have products where you can set when you want your policy to start.

But yeah, our website is an imperative part of our marketing funnel. I think our brand is super unique—most people probably wouldn’t have guessed that a big insurance company, one of YC’s top companies, is using cartoon birds as their primary brand element.

But I actually love it. It’s super memorable. It gives us a lot of opportunities to create fun animations that make our website more engaging.

Our website is super important to us and I genuinely believe our design team is world class. If you go to our website, there are so many things you won’t even notice the first time. I was working here for three months before I noticed certain small animations happening on the page that keep you engaged even if you don’t realize why you’re so tuned in.

So yeah, we spend a lot of time honing our aesthetic and our brand.

Rick: There’s definitely a contrast with legacy insurance websites. And it fits the audience—more free-spirited, on the go, loving adventure. And it’s not typically what you associate with insurance, so it really stands out.

Joey Flores: It’s a big differentiator for us. And internally we think about it—birds represent migration, they represent mobility, so it’s definitely on brand for the kind of customers we work with.

Rick: Joey, I want to switch gears and talk about you as a leader. What does a typical workday look like for you and what do you focus on day to day at SafetyWing?

Joey Flores: If you ask me that question six months from now, it’ll be very different. I just joined, I haven’t even been on the job for four months.

The company is primarily product-led. We have four different product teams: one on the B2B side, and then different consumer products. Historically they’ve done their own marketing—building landing pages, email flows, and things like that.

And now I’m the first head of marketing the company has ever had. So I’m trying to centralize a lot of those functions. Right now it’s about getting alignment with the teams, figuring out what everybody’s working on, and what marketing should take over immediately versus transition over time.

So right now I’m building out the marketing department from the ground up and figuring out how a centralized marketing department can work in an otherwise decentralized organization. So it’s a lot of process, ops, and general strategy.

In six months, when I have a team in place, I may be spending time differently. But for now, it’s organizing how the organization will function with marketing now in place.

Rick: That sounds exciting and also a lot of work. But a great opportunity to set the standard. Do you have time to keep up with trends, inspiration, learning—or do you mostly learn on the job?

Joey Flores: I lean more towards on the job. I love to try things, experiment, learn, and use intuition plus data to make decisions.

If there’s a channel I need to understand better—GEO is one—I’ll use LLMs to do heavy research. I’ll dive into ChatGPT and ask things like: how does optimization work for this channel? What engagement metrics matter? What are people doing that’s interesting?

I don’t really follow a lot of newsletters, but I frequently use LLMs for research. And I lean toward experimentation—figuring it out by doing.

Rick: That’s the entrepreneurial spirit. Now, we have a rapid fire segment. Ready for it?

Joey Flores: Sounds good.

Rick: When it comes to consuming content, what format do you prefer—watching, reading, or listening?

Joey Flores: Watching. I definitely watch a lot of content—probably on YouTube. Not a big reader.

Rick: What’s the latest piece of content you watched, and did anything stick with you?

Joey Flores: The truth is, I just watched way too much Shark Tank. I find it so riveting to listen to these people. It’s addictive in this format. But I feel like I learn a lot from it. Maybe not all applicable to online businesses—there’s a lot of consumer packaged goods—but I do feel like I learn new things quite often. It’s a weird one to reference as learning, but it is what I watch the most.

Rick: You can learn how to tell people their ideas suck in different ways.

Joey Flores: Exactly—take it behind the barn and shoot it.

Rick: If you had a magic wand and could fix one frustrating thing in your marketing life with tech, what would you pick?

Joey Flores: An AI-driven analyst would be interesting—not just something where I can ask questions. A lot of times you notice something in data and then you have to pull threads: why is this segment different, what’s driving it?

But you have to know what questions to ask. It would be interesting if a system with access to your data did the question asking and digging for you, and surfaced insights. In my experience, you usually have to know what you’re looking for. It’d be cool if something could ask better questions than you.

Rick: Love that—finding the right question. What’s one repetitive task you’d love to put on autopilot forever?

Joey Flores: Politely responding to emails and LinkedIn messages that I’m not interested in. I tend to still reply, which is probably a waste of my time. If I could have something that writes back like, “Thanks for reaching out, but I can’t prioritize this right now,” that would be great.

Rick: There has to be something for that.

Joey Flores: Yeah, maybe if I spent more time reading and less time watching Shark Tank, I would’ve found it already.

Rick: Joey, thank you for being on the show. As we wrap up, I want to give you the last word. If someone forgets everything about today, what’s the one thing they should remember about what you’re building?

Joey Flores: We have a big vision for how to make borderless and global living easier and safer. What we’re doing today in terms of insurance is just the tip of the iceberg. We’re looking at income protection, pension programs—all the things that would make you feel comfortable moving somewhere else and setting up your life there.

Check out SafetyWing for what we have today, but also keep us in mind if you’re thinking about a more global future, because we’re focused on creating an all-encompassing safety net that keeps people secure no matter where they are in the world.

Rick: If people want to check out your products, where should they go?

Joey Flores: www.SafetyWing.com

Rick: Too easy. Joey, thank you again for your insights. Hopefully we can do this again soon in 2026 when the team is built and things are growing—see what changed. And maybe you’ll get even more time to watch Shark Tank.

Joey Flores: Sounds good. That would be really good.

Rick: In the meantime, I wish you a beautiful day. This will be out in a few weeks, but Merry Christmas or Happy Holidays.

Joey Flores: Likewise. Happy holidays, Rick.

Rick: Amazing. Take it easy. Thank you guys. Bye.

Joey Flores: Bye.