A turbulent flight sparked Wayne Slavin’s idea for Sure: let consumers buy insurance in real time. But after launching as a D2C app, he realized the bigger opportunity was powering insurance sales for others. Sure’s pivot to B2B turned it into a vertical SaaS platform that lets enterprise companies embed insurance at the point of transaction.
In this episode, Wayne explains how to pivot without losing your mission, why founders should lead early enterprise sales, and why he refuses to run proof-of-concept deals. He also shares why — if he could do it over — he’d avoid launching a business with so much built-in complexity.
RUNTIME 51:58 EPISODE BREAKDOWN(3:16) How a turbulent flight inspired Wayne to sell insurance directly to consumers.
(7:03) Why he reached out to a founder who tried (and failed) to launch an insuretech startup.
(12:01) Becoming fluent in insurance industry jargon “was definitely a learning curve.”
(16:05) The point when Wayne realized Sure needed to pivot.
(20:16) The transition from D2C to B2B “was a slow aircraft carrier style turn.”
(22:35) How to tell whether you’re grinding through a rough patch or building on the wrong model.
(29:21) When it was time to pitch to enterprise customers, “ most of those conversations were led by me.
(32:40) “ Proofs of concept are actually the way for a big company to not do something.”
(40:45) Sure is an embedded finance company, not an insurance company.
(44:04) “ In hindsight, I would not want to be in another business where you are dependent on two other parties performing.”
(49:08) The one question Wayne would have to ask the CEO if he were interviewing for a role with an early-stage startup.
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Thanks for listening!
– Walter.
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