a16z|Oct 26, 2026 18:17
Kyle Norton met with 30 to 40 vertical AI founders before deciding where to go next, and he chose to become CRO of @LassieAI.
He first met Lassie's founders as an advisor, telling them their traction was strong enough to hire a real CRO, before coming back a few weeks later wanting the job himself.
What sold him:
- Retention that looked like a Series D company's, from SMBs on month-to-month contracts
- Founders who did back-office admin work alongside small business owners before writing a single line of code
- Almost entirely organic growth, from a 15-person team with no marketing function and just three people selling
"My thesis with Lassie was, they solved the hardest, most high-trust, high-credibility, most difficult problem in the healthcare practice, which is managing their money. Getting them paid."
Kyle is looking for obsessive learners with a history of excellence, long-term players, and builders who root for the little guy, the independent practices and small businesses Lassie serves.
Lassie is hiring across GTM, engineering, ops, finance, and design: https://a16zjobs.substack.com/p/kyle-norton-prev-shopify-owner-is
@kylecnorton @steijnpelle @fredericrenken
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