Bret Taylor of Sierra on AI agents, outcome-based pricing, and the OpenAI board

Bret Taylor of Sierra on AI agents, outcome-based pricing, and the OpenAI board – Cheeky Pint

Market views

Bullish

SIERRA— Sierra is experiencing explosive growth with $165M ARR in 8 quarters, helping companies build AI agents for customer experience with strong outcome-based pricing model.
AIAGENTS— AI agents are becoming the primary digital interface for businesses, with mainstream adoption expected in 2026 as they handle sales, service, and customer experience end-to-end.
ROCKET— Rocket Mortgage is transforming the home ownership experience end-to-end with AI agents, from home search on Redfin to mortgage origination and servicing.
GOOGL— Google Maps creator Brett Taylor is bullish on AI adoption and Sierra's integration with major enterprises, suggesting continued innovation in AI services.

Bearish

SAAS— Software companies face existential threat as AI agents may replace systems of engagement and companies will build rather than buy software.
HANDCODING— Manual coding is becoming obsolete as AI agents take over software development, with most Silicon Valley companies expected to stop hand-coding by end of 2026.

Not investment advice.