Sure CEO Wayne Slavin recently appeared on the BUILDERS podcast, hosted by Brett Stapper, to share how Sure pivoted from consumer mobile app to B2B infrastructure. The shift happened because insurance executives couldn't stop pulling their engineering teams into meetings to examine Sure's backend operations.
Minimal investment testing of market demand
Wayne's approach to demand validation offers a template for founders in regulated industries. Wayne started with zero insurance experience but a clear hypothesis: people want to buy insurance online when they need it. Ten years ago, he built a prototype over one weekend and ran paid ads to test demand.
The 15.91% conversion rate from ad click to purchase validated the market before committing to regulatory processes. That single metric justified spending his first year navigating carrier partnerships as a solo founder.
The real product reveal
Sure originally pitched itself as a consumer-facing mobile app. Wayne would demo the interface to insurance C-suites, who responded with polite interest about new distribution channels.
Then, something changed. After Wayne would show the backend infrastructure of how the app worked, executives would call their own engineers into the boardroom saying, “We are spending hundreds of millions of dollars to try and figure this out. And these guys have figured it out already.”
The pattern repeated. Prospects would nod through the app demo, then lean forward when they saw the operations infrastructure platform. The energy shifted completely.
After multiple meetings where prospects ignored the app but examined the backend systems intensely, Wayne recognized the signal. The infrastructure solving Sure's consumer business was what insurance companies actually needed.
“That’s when we realized, wait a second, we’re not going to be the marketing gurus, but we can be the tech gurus to do this.”
Three failure modes create the best customers
Sure's ideal clients aren't greenfield opportunities. They're companies that experienced specific failures:
Internal builds that collapsed when engineers left. Projects fell apart when key developers moved on, taking institutional knowledge with them.
Direct carrier partnerships that violated platform principles. Brands discovered they had to rebuild integrations for each carrier relationship.
Multi-carrier tools that created analysis paralysis. More options overwhelmed customers instead of improving experience.
Wayne explicitly avoids prospects choosing to build internally. Companies selecting build options don't understand their environment. Sure marks these as "on hold" until failure brings them back.
Understand enterprise buyer psychology
Wayne identified a critical insight about enterprise buying behavior: large company decision-makers face misaligned incentives when evaluating solutions. Leading internal builds looks impressive from a career perspective, but buyers unknowingly trade stable budgets for execution risk. In enterprise environments, execution risk ends careers.
Large companies pay Salesforce billions not because everyone loves the product, but because it works consistently. It's about stable IT projects that deliver expected outcomes. The lesson for B2B founders: help enterprise champions articulate how buying solutions protects their job security rather than just emphasizing product superiority.
Becoming insurance chameleons
Sure's differentiation isn't performance metrics. Wayne describes Sure’s team as "chameleons" who match each partner's exact corner radius, modal behavior, and loader effects. This obsessive attention to UX details means product teams don't fight the insurance insertion.
This enables customers to complete insurance purchases without touching their keyboard. All information pre-fills from partner data. All interactions match existing patterns.
Most embedded solutions force brands to choose between functionality and consistency. Sure eliminates this choice.
Sure is sticking around for the long game
Sure will continue to read the room. Wayne's thesis: the next twenty large insurance businesses will be built by consumer brands, not traditional carriers. These brands have the relationships to win but won't build infrastructure themselves. That’s where Sure comes in. The opportunity isn’t building another insurance carrier, it’s providing the technology rails that let brands with millions of customers become insurance businesses without spending a decade building infrastructure themselves.
Pattern recognition over planning
Wayne's insights reveal how careful observation of buyer behavior can uncover opportunities larger than original product visions. The key is listening to what genuinely excites prospects, building solutions that reduce risk for decision-makers while seamlessly integrating into existing workflows.
