

EP 150: Bret Taylor (CEO, Sierra): A New Class of Software Winners
109 snips Sep 12, 2025
Bret Taylor, CEO of Sierra and former co-CEO of Salesforce, shares insights on the ongoing AI revolution. He compares AI to past technological shifts, highlighting its impact on startups and established companies. The discussion delves into innovative pricing strategies and how AI is reshaping value creation. Taylor also explores challenges in adopting AI, the changing landscape of enterprise software, and the democratization of software development. Plus, he offers career advice for navigating the AI-driven future.
AI Snips
Chapters
Books
Transcript
Episode notes
Fundraising As A Milestone
- Bret frames raising a round as a milestone and fuel for a long journey building a durable company.
- He emphasizes sustained execution is required to 'write the history book' in AI.
AI Echoes The Internet Battle
- Bret compares the AI wave to the internet era where obvious categories like search and e-commerce were early battlegrounds.
- He warns that product form factors, business models, and packaging will determine which companies win.
Agents Reframe Software Value
- Agents change what 'software' means by actually doing work, expanding addressable markets like legal advice.
- Valuation shifts from productivity metrics toward direct business economics like margin and commission equivalents.