Decagon’s 10x year:how Jesse Zhang scaled the team without lowering the bar
Key points
Key takeaways from the Grit interview with Decagon co-founder and CEO Jesse Zhang, recorded at Kleiner Perkins, September2026:
Scaling from 50 to 500 in a year. Decagon roughly 10xed its team over the past year, running more than2,000 interviews; Jesse Zhang and co-founder Ashwin Sreenivas personally met every candidate up to about300 people, then handed bar-raising interviews to a trusted inner circle to keep the bar high, a practice they borrowed from Revolut and Amazon.
Conservative hiring early, hiring ahead now. For the first 18 months the pair hired only when the pain of a missing role became acute, keeping the team around 50-60 and never hiring ahead of demand; in hindsight Zhang says they could have been bolder, but hiring ahead before demand closes is now unavoidable when scaling this quickly.
PMF in three weeks with six customers. Unlike the long idea maze of his previous startup, Decagon found product-market fit quickly, and Zhang draws a sharp line between the zero-to-one phase and scaling — at 500 people, the company feels like "a new company every quarter or two", with processes constantly reinvented.
Why he won’t found solo again. As the solo founder of Lowkey, acquired by Niantic in 2021, Zhang felt like the single point of failure,and had no peer with equal context and commitment to bounce ideas off, slowing ideation dramatically; he now uses Claude as an AI sounding board,and says having co-founder Ashwin makes it "10x easier", with Decagon built in-person after his COVID-era remote experience.
Differentiation from Sierra. Zhang frames Decagon’s edge over Sierra,Bret Taylor’s customer-service agent company, as an edge in product deployment:the AI is built in, tested in,and monitored inside the product, so the customer owns the outcomes,and the process — "building an agent that can’t afford to get it wrong".
One big rectangle to keep 500 people connected. Decagon deliberately uses large, open office spaces — Zhang cites the goal of "500 people in one rectangle" — to fight the isolation that creeps into office layouts as the team sprawls across SF, New York(three offices in less than a year), London,and a newly announced Australia hub.
Everyone is making it up — even the greats. Zhang takes comfort in noting that seasoned operators like Marc Benioff, Arvind Jain,and Bret Taylor have never run a company at this size,in this moment,in this technology wave — so every founder is effectively learning in public, as Decagon does.
Read more: Grit (Kleiner Perkins)
