In this episode of Frameworks for Growth, Vanta CEO Christina Cacioppo sits down with Bret Taylor, Co-founder of Sierra, to discuss the evolution of technology, from the early days of cloud at Salesforce, to enterprise-ready AI companies—plus cultural lessons from companies like Google and Facebook, and what it takes to launch successful AI startups today.

Bret shares insights from decades at the forefront of tech innovation—including his time as co-CEO of Salesforce and CTO of Facebook—offering advice for founders navigating today’s market and tomorrow’s challenges.

🔑 Topics covered (timestamps): 

00:11 - Introduction

01:00 - Building websites and the birth of a career

02:28 - Yahoo Directory and the shift to AI-driven experiences

03:40 - What Sierra does and how it powers brands with AI agents

04:34 - Comparing AI evolution to past tech waves

05:45 - Frameworks still missing for building AI agents

06:30 - Democratizing access to AI tools for all companies

07:36 - Competitive moats in the AI market

08:54 - AI value chain: from models to airport-priced lattes

11:00 - Innovation pace vs. shipping outcomes

13:23 - Business models built around outcomes, not effort

15:53 - Customer alignment and predictable pricing at Sierra

17:40 - What people may get wrong about AI and productivity

19:00 - Economic realities: intelligence isn't the only bottleneck

20:25 - The early days of Google Maps and why it went viral

23:00 - Integrating content into Maps—and being name-dropped on SNL

24:19 - What makes a great board member (and a cohesive board)

26:49 - Founders and board dynamics: trust, motivations, and self-awareness

28:10 - Operator vs. investor board members

30:03 - Leadership styles from Benioff, Zuckerberg, Marissa Mayer, and more

32:22 - Customer obsession at Sierra and real accountability

34:59 - How Sierra plans for rapid shifts in AI tech

37:23 - Why model maintenance is a massive challenge

38:45 - Bret’s worst tech predictions (no self-driving, too much tablet optimism)

41:00 - There’s no one-size-fits-all leadership style

43:41 - The startup machine that produces happy customers

45:11 - Founder focus: how to know where to spend your time

47:12 - Founding Sierra during the ChatGPT boom

49:00 - Writing a choose-your-own-adventure app for his daughter

50:54 - Why Sierra started with enterprise customers

53:15 - How AI changes the economics of customer support

54:07 - Frameworks for go-to-market: PLG, dev-first, direct sales

58:30 - Selling software is a spreadsheet, not just a steak dinner

59:08 - Enterprise-first strategy and choosing design partners

01:02:18 - What makes a good design partner

01:02:20 - Lightning round: Ben Franklin, VR skepticism, and Clubhouse fizzle

01:04:45 - Wrap-up and closing thoughts