Enhancing AI-Customer Interactions Through Context and Automation

Bret Taylor’s legendary career includes being CTO of Meta, co-CEO of Salesforce, chairman of the board at OpenAI (yes, during that drama), co-creating both Google Maps and the Like button, and founding three companies. Today he’s the founder and CEO of Sierra, an AI agent company transforming customer service. He’s one of the few people I’ve met who’s been wildly successful at every level—from engineer to C-suite executive to founder—and across almost every discipline, including PM, engineer, CTO, COO, CPO, CEO, and board member.

In this conversation, you’ll learn:

1. The brutal product review that nearly ended his Google career—and how that failure led to creating Google Maps

2. The question Sheryl Sandberg taught him to ask every morning (“What’s the most impactful thing I can do today?”) that transformed how he approached every role

3. The three AI market segments that matter

4. Why AI agents will replace SaaS products

5. His framework for knowing whose advice to actually listen to—and how that came in handy during the OpenAI board drama

6. The counterintuitive go-to-market strategy most AI startups get wrong

7. Sierra’s outcome-based pricing model that’s transforming how enterprise software is sold (and why every SaaS company should adopt it)

8. What he’s teaching his kids about AI that every parent should know

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Transcript: https://www.lennysnewsletter.com/p/he-saved-openai-bret-taylor

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My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/168905359/my-biggest-takeaways-from-this-conversation

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Where to find Bret Taylor:

• X: https://x.com/btaylor

• LinkedIn: https://www.linkedin.com/in/brettaylor/

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Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

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In this episode, we cover:

(00:00) Introduction to Bret Taylor

(04:10) Bret’s early career and first major mistake

(08:24) The birth of Google Maps

(11:57) Lessons from FriendFeed and the importance of honest feedback

(31:30) The future of coding and AI’s role

(45:26) Preparing the next generation for an AI-driven world

(48:46) AI in education

(52:05) Business strategies in the AI market

(01:04:38) Outcome-based pricing in AI

(01:09:15) Productivity gains and AI

(01:17:35) Go-to-market strategies for AI products

(01:21:49) Lightning round and final thoughts

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Referenced:

• Marissa Mayer on LinkedIn: https://www.linkedin.com/in/marissamayer/

• “Lazy Sunday”—SNL: https://www.youtube.com/watch?v=sRhTeaa_B98

• Quip: https://quip.com/

• Sierra: https://sierra.ai/

• FriendFeed: https://en.wikipedia.org/wiki/FriendFeed

• Sheryl Sandberg on LinkedIn: https://www.linkedin.com/in/sheryl-sandberg-5126652/

• Jim Norris on LinkedIn: https://www.linkedin.com/in/halfspin/

• Paul Buchheit on X: https://x.com/paultoo

• Sanjeev Singh on LinkedIn: https://www.linkedin.com/in/sanjeev-singh-20a1b72/

• Barack Obama: https://www.obamalibrary.gov/obamas/president-barack-obama

• Oprah Winfrey: https://en.wikipedia.org/wiki/Oprah_Winfrey

• Ashton Kutcher: https://en.wikipedia.org/wiki/Ashton_Kutcher

• PayPal Mafia: https://en.wikipedia.org/wiki/PayPal_Mafia

• Sam Altman on X: https://x.com/sama

• Warren Buffett on X: https://x.com/warrenbuffett

• Unix: https://en.wikipedia.org/wiki/Unix

• Fortran: https://en.wikipedia.org/wiki/Fortran

• C: https://en.wikipedia.org/wiki/C_(programming_language)

• Python: https://www.python.org/

• Perl: https://www.perl.org/

• Rust: https://www.rust-lang.org/

• Eleven Labs: https://elevenlabs.io/

• The exact AI playbook (using MCPs, custom GPTs, Granola) that saved ElevenLabs $100k+ and helps them ship daily | Luke Harries (Head of Growth): https://www.lennysnewsletter.com/p/the-ai-marketing-stack

• Confluent: https://www.confluent.io/

• Databricks: https://www.databricks.com/

• Snowflake: https://www.snowflake.com

• Harvey: https://www.harvey.ai/

• Behind the founder: Marc Benioff: https://www.lennysnewsletter.com/p/behind-the-founder-marc-benioff

• Larry Summers’s website: https://larrysummers.com/

• AutoCAD: https://www.autodesk.com/products/autocad/overview

• Revit: https://www.autodesk.com/products/revit/

• The art and science of pricing | Madhavan Ramanujam (Monetizing Innovation, Simon-Kucher): https://www.amazon.com/Monetizing-Innovation-Companies-Design-Product/dp/1119240867

• Pricing your AI product: Lessons from 400+ companies and 50 unicorns | Madhavan Ramanujam: https://lenny.substack.com/p/pricing-and-scaling-your-ai-product-madhavan-ramanujam

• Cursor: https://cursor.com/

• CodeX: https://openai.com/codex/

• Claude Code: https://www.anthropic.com/claude-code

• The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell

• DirecTV: https://www.directv.com/

• SiriusXM: https://www.siriusxm.com/

• Wayfair: https://www.wayfair.com/

• Akai: https://www.akaipro.com/

• Chubbies Shorts: https://www.chubbiesshorts.com/

• Weight Watchers: https://www.weightwatchers.com/

• CLEAR: https://www.clearme.com/

• Stripe: https://stripe.com/

• Building product at Stripe: craft, metrics, and customer obsession | Jeff Weinstein (Product lead): https://www.lennysnewsletter.com/p/building-product-at-stripe-jeff-weinstein

• Twilio: https://www.twilio.com/

• ServiceNow: https://www.servicenow.com/

• Adobe: https://www.adobe.com/

• Jobs to be done: https://jobs-to-be-done.com/jobs-to-be-done-a-framework-for-customer-needs-c883cbf61c90

• The ultimate guide to JTBD | Bob Moesta (co-creator of the framework): https://www.lennysnewsletter.com/p/the-ultimate-guide-to-jtbd-bob-moesta

• Inception: https://www.imdb.com/title/tt1375666/

• Alan Kay’s quote: https://www.brainyquote.com/quotes/alan_kay_100831

• Jobs at Sierra: https://sierra.ai/careers

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Recommended books:

• Monetizing Innovation: How Smart Companies Design the Product Around the Price: https://www.amazon.com/Monetizing-Innovation-Companies-Design-Product/dp/1119240867

• Competing Against Luck: The Story of Innovation and Customer Choice: https://www.amazon.com/Competing-Against-Luck-Innovation-Customer/dp/0062435612

• Endurance: Shackleton’s Incredible Voyage: https://www.amazon.com/Endurance-Shackletons-Incredible-Alfred-Lansing/dp/0465062881

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Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.