10 Mar 2026
1h 41m

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

Podcast cover

Cheeky Pint

The discussion centers on the transformative impact of AI on software engineering, customer service, and broader business strategies. It highlights the shift towards AI agents handling customer interactions across multiple channels, exemplified by Sierra's work with companies like SoFi and Rocket Mortgage. A key insight is the potential for AI to drive better customer experiences and reduce churn by making customer service more accessible and efficient. The conversation also explores how AI is changing the structure of software companies, potentially elevating the role of generalists who deeply understand customer needs. Bret Taylor shares his experiences on the Twitter and OpenAI boards, and offers predictions for 2026, including scientific breakthroughs enabled by AI and widespread adoption of AI-driven code generation.

Outlines

Part 1: AI Development, Coding, and Documentation

Part 2: Agentic Commerce and Infrastructure

Part 3: Sierra Case Study and Customer Experience

Part 4: Business Strategy and Market Dynamics

Part 5: Pricing Models and Value Alignment

Part 6: Productivity and Organizational Change

Part 7: Leadership, Governance, and Future Outlook

Sign in to continue reading, translating and more.

Open full episode in Podwise