Uncapped #42 | Bret Taylor from Sierra

Uncapped #42 | Bret Taylor from Sierra

1:00:37 Feb 19, 2026
About this episode
Bret Taylor is the founder and CEO of Sierra, an AI agent company transforming customer service. Bret’s legendary career includes being CTO of Meta, co-CEO of Salesforce, chairman of the board at OpenAI, co-creating both Google Maps and the Like button, and founding three companies. We unpacked the so-called “SaaS-pocalypse” and what AI agents mean for the future of enterprise software. We talked through the shift from systems of record to autonomous agents, outcome-based pricing, platform transitions, Codex and the transformation of software engineering, and who is structurally positioned to win in the next era of AI. --- Timestamps: (0:00) Intro (0:20) The SaaS-pocalypse and systems of record (12:34) Sierra's competitive landscape (17:05) Outcomes-based pricing (24:22) The rapid evolution of AI support technology (28:21) Young founders vs. experienced founders (34:12) Beyond support: The full customer lifecycle (38:47) Codex and the future of software engineering (51:49) OpenAI and advertising (54:59) How to run a board --- Links: https://x.com/btaylor https://x.com/jaltma https://uncappedpod.com/ --- Email: friends@uncappedpod.com
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