5 Questions with FinTech Founders - Sure

April 24, 2024
by: Cohen Circle Team

Welcome to 5 Questions with FinTech Founders, where we sit down with the next generation of FinTech innovators to hear about how they got started, and where they are going. 

In this installment, we spoke with Wayne Slavin, CEO and Co-Founder of Sure, the global insurance technology leader that unlocks the potential of digital insurance.

A seasoned entrepreneur, Wayne stays at the forefront of innovation by creating disruptive technologies that improve the customer experience for industries relying on legacy tech stacks. 

His credentials include several successful exits. Wayne founded the SaaS company BackupRight, which sold in 2012. He was the first employee and VP of Product Management at Tapingo, named the Most Innovative Company of 2013 by TechCrunch. Wayne’s achievements are further enhanced by roles at mobile app NetSlumber, Barnes and Noble, and Buddy Media, which was acquired by Salesforce. He earned his MS from Columbia University in New York City.

1. What inspired you to start Sure?

Sure’s journey is not unlike other startups. One idea led to another idea, which in turn led to the creation of Sure. It all started on an airplane. In 2014, I was mid-flight from San Francisco to Las Vegas when we suddenly experienced some pretty serious turbulence. As I was looking around at the other passengers, I could tell it was a really scary experience for them. It dawned on me that there should be an easy way to buy insurance on the spot. In this case, it was the idea of purchasing life insurance before boarding a flight. 

So we built a proprietary app for people to purchase insurance quickly and frictionlessly, starting first with flight insurance, baggage insurance, and shortly after smartphone insurance, to name just a few. We then realized that the technology we developed was so powerful that the opportunity for Sure was so much bigger. Instead of selling insurance digitally ourselves, we could use our technology to help others sell insurance online. Sure is now entirely focused on combining our insurance expertise with our technology as a Software as a Service solution to power the digital insurance programs of large brands and carriers, including the likes of Toyota, Mastercard, and Farmers Insurance. 

2. What problem were you trying to solve in the market?

Today’s consumers have proven that they want to buy insurance differently – they want the right product, at the right time, in the right place. The truth is that the large, legacy insurers haven’t been able to deliver the types of experiences consumers now expect. The biggest challenge with embedded insurance is having the technology expertise to build these new digital insurance experiences. While large carriers obviously have the insurance expertise, they don’t always have the technology expertise to deliver these experiences quickly and at scale.  

That’s where Sure comes in. For us, unlocking the potential of digital insurance means that we are able to help our partners solve the complex problems of digital insurance distribution. That means bringing the entire end-to-end journey of not only the application, rate, quote, and bind process, but also policy administration and claims into the digital age. We provide the rails to enable our partners to reach people where they are and deliver world-class customer experiences. 

3. Describe a time when you needed to course correct.

When we started Sure, we really looked at the market and made some pretty good guesses about what would and wouldn't work. We knew very early on that we were always going to be multi-line and sell every type of insurance. At that time, existing options in the market were focused around D2C mobile apps that also had some embedded distribution — but the experience was all controlled by the mobile app of the company.  

We built the SaaS infrastructure for the distribution problem, because nothing like it existed. We quickly realized that we're not a marketing company, and that we needed to play to our team’s strengths. It was pretty clear that, given our team's experience, we were going to be the best at building complex software.  

Changing course away from a D2C strategy to becoming an insurtech infrastructure company was an evolution, not the result of one meeting. Importantly, I didn't pull the plug on a thing that was working until we'd proven we could do the other thing. Some startups prematurely pivot — but we took an aircraft-carrier style turn instead of a pivot. We did what we set out to do while going out and finding our first customers for our SaaS solution. 

The results speak for themselves: The first deal we ever closed as an infrastructure provider is still going, nine years later. It just worked, and we made sure that our team felt supported in that transition.  

4. What advice would you give to new entrepreneurs on raising capital? 

The tech industry, and SaaS specifically, has been a rollercoaster the last couple of years. Startups have had to evolve rapidly from a sustained period of growth and readily available capital followed by a challenging macroeconomic climate. That said, there is a major flight to quality. Quality companies, even ones that require substantial investment, are still able to raise capital at attractive valuations. I believe there is a lot of innovation taking place for investors to be excited about, and that emerging technologies like generative AI will continue to expand growth opportunities for new entrepreneurs raising capital.  

In the insurtech space specifically, there are so many opportunities for companies to further innovate and bring a centuries old industry out of the stone age and into the digital age. As I speak with insurtech investors who reach out to us, they are looking for companies that have found the sweet spot of combining insurance with technology to make buying and managing of insurance seamless. 

5. What lessons have you learned that you would share with other entrepreneurs looking to scale? 

Mentors can be an invaluable resource in founding and scaling a business. When I started my first SaaS business and didn't see a perfect, hockey-stick J-curve, I thought: "Somebody out there knows how to do that. What didn't I do that other people did that would've caused a different result?" As founders, we know that sometimes you build a great product, but there can be so many reasons why it doesn’t win the market.  

So when I first founded a company, I knew how to build a product and how to support it, but I also knew I had knowledge gaps in other areas. So I went looking for people who knew what I didn't know: What insights were missing from my universe? This curiosity has carried with me as I’ve progressed in my career, from successfully founding and exiting companies to building our team and products at Sure. Being self-reflective enough to know that I could still learn from other people has been really meaningful in helping me grow our business at Sure, but also in growing as a founder and as an entrepreneur.  

To learn more about Sure visit

more insights

Helping Accelerate Fintech Growth Companies Through Investments And Resources

Read more

Girls into VC

Read more

5 Questions with FinTech Founders - Sure

Read more
 Read about
the launch of
Cohen Circle logo
linkedin facebook pinterest youtube rss twitter instagram facebook-blank rss-blank linkedin-blank pinterest youtube twitter instagram