Ep 311: Wayne Slavin, CEO & Co-Founder, Sure

In Episode 311 of the FNO: InsureTech Podcast, hosts Lee Boyd and David Prejeant sit down with Wayne Slavin, CEO and Co-founder of Sure, for a conversation that spans embedded insurance, AI, digital distribution, and the future of insurance innovation. What begins with a story about turbulence on a flight quickly evolves into a fascinating discussion about how insurance can become a seamless part of everyday consumer experiences. 

Founded in 2015, Sure has built an AI-enabled platform that helps some of the world's largest carriers and consumer brands launch and operate fully digital insurance programs. Today, companies like Toyota, Zillow, and Mastercard leverage the platform to integrate insurance directly into their customer experiences. 

Wayne shares his journey from Silicon Valley product development and e-commerce innovation into insurance, explaining how his early experience building consumer technology shaped his belief that insurance should be as easy to access as any other digital transaction. 

The conversation also explores Wayne's long-standing interest in AI, dating back more than 16 years, his perspective on where AI creates the most value in insurance, and why the industry's biggest challenge may not be technology at all, but change management. 

Whether you're interested in embedded insurance, digital transformation, AI, or simply hearing the founder story behind one of InsureTech's most recognized platforms, this episode delivers valuable insights and bold predictions about where the industry is headed next. 

Key Highlights

[06:00] Meet Wayne Slavin and Sure

Wayne introduces Sure and explains how the company helps carriers and consumer brands launch fully digital insurance programs through a single end-to-end platform. 

[08:00] The Visa of Insurance

Wayne explains Sure's role as a technology platform, connecting carriers, brands, and consumers without acting as the insurer itself. 

[10:00] Why Insurance Needs an End-to-End Ecosystem

A discussion on the fragmented nature of insurance technology and why Sure chose to build a unified platform rather than another point solution. 

[12:00] The Turbulent Flight That Started It All

Wayne shares the origin story behind Sure and how a turbulent flight sparked the idea of making insurance available at the exact moment consumers need it. 

[17:00] Making Insurance Invisible

Why Wayne believes insurance should become a natural part of other consumer transactions rather than a separate buying experience.

[18:00] Embedded Insurance and the Next Distribution Frontier

How brands can integrate insurance directly into customer journeys and why Sure focuses on meeting consumers where they already are.

[20:00] AI Before It Was Cool

Wayne reflects on researching human-in-the-loop AI at Columbia more than 16 years ago and why today's AI revolution is a moment he has anticipated for years. 

[22:00] Where AI Delivers Real Value

A practical discussion on why AI is creating the biggest gains in speed to market, customer service, claims support, and operational efficiency. 

[24:00] Going Live in Days, Not Months

How Sure is leveraging AI and automation to dramatically reduce implementation timelines and operational complexity. 

[26:00] Learning the Insurance Business

Wayne shares how curiosity, study, and starting with simple insurance products helped him navigate an industry he originally knew nothing about.

[30:00] AI Adoption Is a Leadership Challenge

Why some insurers are embracing AI while others remain hesitant, and how leadership mindset often determines success. 

[32:00] The Real Bottleneck: Change Management

Wayne argues that technology is no longer the limiting factor. The bigger challenge is changing inherited processes and organizational behavior. 

[34:00] The Future of Direct-to-Consumer Insurance

A discussion on changing consumer expectations, digital buying experiences, and why convenience matters more than ever. 

[39:00] From South Africa to Silicon Valley

Wayne reflects on his personal journey, his family's move to the United States, and how those experiences helped shape his entrepreneurial path.

[40:00] What's Next for Sure

Wayne shares his vision for the future, including making it even easier for large brands to launch insurance businesses with minimal friction.

[42:00] Final Thoughts

Lee and David reflect on Wayne's unique founder story, deep technology background, and the future opportunities ahead for Sure and embedded insurance.