Bret Taylor

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.

14 skills 23 insights

AI & Technology Skills

The AI market is divided into CapEx-heavy frontier models, risky tooling, and high-value applied agents that solve specific business problems.

"I think there's three segments of the AI market... frontier model market... tooling... applied AI market. I think this will play out for companies who build agents. I think agent is the new app."
52:36

The future of software is autonomous agents that are priced based on the value they deliver rather than the seats they occupy.

"The whole market is going to go towards agents. I think the whole market is going to go towards outcomes-based pricing. It's just so obviously the correct way to build and sell software."
59:31

Coding is shifting from manual syntax writing to the high-level operation and supervision of AI systems.

"I think the act of creating software is going to transform from typing into a terminal... to operating a code-generating machine."
31:47

Robustness in AI applications is achieved by layering multiple models to review and reflect on each other's work.

"Having AI supervise the AI is actually very effective... you can layer on more layers of cognition and thinking and reasoning and produce things increasingly robust."
01:10:10

Most LLM failures are context failures; the solution is 'context engineering' rather than just waiting for better models.

"If a model making a poor decision, if it's a good model, it's lack of context... fix it at the root is the principle here."
01:13:41

When evaluating emerging tech like AI, focus on systems thinking and foundational principles rather than just current tools.

"I do still think studying computer science is a different answer than learning to code... computer science is a wonderful major to learn systems thinking."
31:47

Career Skills

To get value from mentors, you must deconstruct their advice into the underlying frameworks to avoid misapplying their specific anecdotes.

"When you ask for advice, don't just ask what to do but why. Be an obnoxious two-year-old kid, why? Why? Why? Why? And really try to understand the framework that someone is using to give you advice."
29:26

Growth Skills

AI software is shifting from charging for usage (tokens) to charging for specific business outcomes, aligning vendor incentives with customer value.

"The whole market is going to go towards outcomes-based pricing. It's just so obviously the correct way to build and sell software."
00:07

Usage metrics like tokens are poor proxies for value in AI; outcomes-based pricing ensures you are paid for the actual problem solved.

"I think there's a huge difference between outcomes-based pricing and usage based pricing because especially in AI, they're not necessarily even correlated... I am a huge believer in this."
01:07:16

Leadership Skills

Leadership requires the courage to have hard conversations about performance and managing out those who don't meet the bar.

"She pulled me into a room and gave me talking to a little bit about holding my team to as high of a standard as I have. If someone wasn't meeting my expectations, what was my plan to manage them out o..."
16:10

Successful career growth requires being receptive to direct, high-stakes feedback from executives and adapting your role to the company's needs.

"I probably credit Sheryl Sandberg for really changing the way I approach new jobs... She pulled me into a room and gave me talking to."
15:09

Avoid the bias of applying your primary skillset as the solution to every problem; the real solution may lie in a different discipline.

"If you're a great engineer, the answer to almost every problem in your business is engineering... you probably by default should question it."
22:14

Marketing Skills

A successful launch often requires a 'sizzle' feature—something visually impressive or viral—to draw people into the core utility.

"With satellite imagery, it honestly wasn't the most important part of Google Maps, but it was the sizzle to the steak and it created... a viral moment."
10:35

Distribution and strategic partnerships (like celebrity adoption) can beat a technically superior product.

"Biz [Stone] was really focused on getting celebrities and public figures onto Twitter... we were exclusively focused on polishing the product... we totally lost for no reason related to product at all..."
25:31

GTM strategy must match the buyer persona; PLG fails when the user and the buyer are different people.

"I think because product-led growth became very popular... if PLG means that you aren't actually engaging with the buyer of your software, you're not going to grow."
01:20:40

Product Management Skills

Breakthrough product visions often come from flipping the traditional hierarchy of information.

"What if we inverted the hierarchy here and made the map the canvas?"
08:49

Competitive analysis should include the 'analog' or non-consumption alternative, not just direct digital competitors.

"Why use this instead of Yahoo Yellow Pages? But more than anything else, why use this instead of the Yellow Pages?"
06:54

Technical superiority and uptime are not enough to win if the competitor has better market momentum or distribution.

"Twitter had the fail whale and it was down half the time... our product, we were innovating faster... and we totally lost for no reason related to product at all."
26:00

Simply digitizing an analog predecessor often fails because it lacks a native reason to exist on the new platform.

"It was a digital version of something that had come before... why use this instead of the Yellow Pages? But more than anything else, why use this instead of the Yellow Pages? It was a digital version..."
06:54

The 'Like' button was born from defining the problem as 'removing low-value one-word comments' to improve discussion quality.

"The original framing was one click comment... we needed a one-click comment. That's where the concept came from."
01:25:48

The Jobs to be Done framework is essential for understanding the underlying need a customer is 'hiring' a product to fulfill.

"Competing Against Luck, which was the book that produced Jobs to be Done, which is a framework I really believe in."
01:21:59

Users often provide 'polite' feedback that masks the true reason for lack of adoption; you must dig for the underlying truth.

"Literally taking what a customer says or what a user says in a focus group or a usability study is rarely correct... it's very important to get right."
21:16

Sales & GTM Skills

Founding is fundamentally a sales role; you must sell the vision to investors, talent, and customers alike.

"To be a great founder, you really need to be able to not have such a ossified view of your identity... you have to sell investors... candidates... customers."
14:17