Podcasts

Sierra CEO & OpenAI Chair Bret Taylor Live at Money2020: AI Bubbles, Software’s Future, & Why Sierra Wins

Ryan Zauk sits down with Bret Taylor, Co-Founder & CEO of Sierra and Chairman of the Board at OpenAI.

13 November 2025

Bret Taylor on Curiosity, Agency, and AI

Ravi Gupta and Shane Battier sit down with tech visionary Bret Taylor, co-founder of Sierra AI, who shares his philosophy on career evolution, explaining why he refuses to let an "ossified version of his past self limit his future self."

23 October 2025

Thought leadership

Clay Bavor featured on the Heart of Healthcare podcast

The Heart of Health podcast: Inside the Rise of AI Agents with Sierra Co-founder Clay Bavor

Most people spend 30+ hours a year dealing with customer service. What if AI could fix that without losing the human touch? Clay Bavor joins us to explore how AI agents are reshaping customer interactions—and what this means for the most complex service industry: healthcare.

20 October 2025

Healthcare

AI made human: How Sierra helps businesses build better experiences in Healthcare

On the Beat podcast powered by HLTH Sierra’s Krishna Bharathala and Isaac Gateño share a practical roadmap—addressing privacy, security, and compliance, choosing high-impact use cases, and navigating the build-versus-buy question in healthcare.

15 September 2025

Healthcare Thought leadership Product

Sierra CEO Bret Taylor on why the AI bubble feels like the dotcom boom

The OpenAI chairman, now working on AI agents at his new startup Sierra, on why the current boom echoes the dotcom era, and how Sierra’s model is built around outcomes, not promises.

11 September 2025

Thought leadership

The Information. Bret Taylor and Winston Weinberg

The AI agents reshaping customer service & law

Bret Taylor from Sierra and Winston Weinberg from Harvey join The Information's Jessica Lessin in an interview on how their startups are disrupting industries, the changing ROI for AI, and what's next for the future of work.

20 August 2025

Thought leadership

1:13:19

How is AI different than other technology waves?

18 August 2025

Thought leadership

AI changing how software is sold. Bloomberg and Bret Taylor

AI changing how software is sold: OpenAI Chairman and Sierra CEO Bret Taylor

Bret Taylor talks about how AI is changing the software sector and the role OpenAI’s board is playing in the company’s restructuring.

15 August 2025

Thought leadership

He saved OpenAI, invented the “Like” button, and built Google Maps: Bret Taylor on the future of careers, coding, agents, and more

Bret Taylor joins Lenny Rachitsky to reflect on his path from Google Maps to the “Like” button, Salesforce, OpenAI, and Sierra. They dig into AI agents, the future of coding, and how work is being reshaped by the next wave of technology.

31 July 2025

Thought leadership

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