Why a seasoned CRO joined LassieAI: Series D-level retention from a 3-person sales team
a16z · x · 2026-10-27
a16z profiles Kyle Norton, who met 30-40 vertical AI founders before joining SMB finance-automation startup LassieAI as CRO.
What sold him:
- Retention resembling 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 code
- Nearly all-organic growth at a 15-person team with just three sellers and no marketing function
His thesis: Lassie solved healthcare practices' hardest, highest-trust problem — getting them paid. He joked his promise to his wife not to do another startup lasted 41 days.
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