Uncapped #42 | Bret Taylor from Sierra

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.
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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
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Links:
https://x.com/btaylor
https://x.com/jaltma
https://uncappedpod.com/
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Email: [email protected]