Cheeky Pint Bret Taylor of Sierra on AI agents, outcome-based pricing, and the OpenAI board
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Mar 10, 2026 
Bret Taylor, Sierra cofounder and CEO and chair of the OpenAI board, dives into AI agents, why software may charge for outcomes instead of seats, and why companies miss the real gains by optimizing org charts instead of processes. He also gets into boardroom turbulence, hyper-generalists, and a future where smartphones may fade as agents become the interface.
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Applied AI Requires Building Things You Plan To Delete
- Bret Taylor says applied AI teams must build capabilities they know will be obsolete soon, because waiting for models to improve means missing the market.
- Sierra built strong Cantonese voice support as a product advantage even though he expects it to be commoditized within a few years.
Agents Threaten SaaS Where Process Matters More Than Data
- Bret Taylor thinks the SaaS selloff is rational because AI creates real uncertainty around where value sits, especially for systems of engagement.
- He argues agents may become systems of record for processes, while traditional databases stay strongest where the record itself is the value, like ledgers.
Outcome Pricing Aligns AI Companies With Customer Value
- Bret Taylor believes outcome-based pricing is more important than usage-based pricing because customers care about business results, not token counts.
- Sierra charges when support cases are fully resolved or sales close, which forces the company to reduce token costs and improve actual performance.