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.

---

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: [email protected]