Podcasts

Agent Development team featured in a healthcare podcast

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.

September 15, 2025

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.

September 11, 2025

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.

August 20, 2025

How is AI different than other technology waves?

August 18, 2025

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.

August 15, 2025

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.

July 31, 2025

Google, Facebook, then Sierra | Bret Taylor

“If there's one lesson I wish I could give my younger self, it's to focus less on the technology and more on the customer need.” Bret Taylor, co-founder of Sierra and chairman of OpenAI.

July 24, 2025

AI special featuring Sierra, Harvey, Windsurf, and more

Six leaders from across tech — from SaaS and semis to law and logistics — come together to unpack how AI are transforming the way industries function, and how work gets done.

July 7, 2025

Bret Taylor’s journey leading Salesforce, Sierra, and OpenAI

Over the past two decades, Bret Taylor has quietly helped shape the arc of Silicon Valley. From co-creating Google Maps to steering Facebook, Salesforce, and OpenAI, he’s been behind some of the most consequential products in tech.

June 2, 2025

Bret Taylor: A vision for AI's next frontier

Bret Taylor, co-founder of Sierra and chairman of OpenAI, explains why the next phase of AI won’t just be about building better models.

April 15, 2025

The AI Architect: Bret Taylor

Bret Taylor discusses how AI is reshaping software development and how the best teams integrate product and engineering while staying deeply technical and customer-focused.

February 11, 2025

TechCheck: with Bret Taylor

Bret Taylor, co-founder of Sierra, joins TechCheck to discuss the era of AI agents and his new startup. Sierra has seen explosive growth, quadrupling its valuation since January to an impressive $4.5 billion

December 6, 2024

Interview with Bret Taylor and Clay Bavor

Squawk Pod: with Bret Taylor and Clay Bavor

Companies like SiriusXM and Sonos are using AI Agents to make customer service experiences “delightful,” thanks to new conversational AI technology from Sierra. The company’s co-founders Bret Taylor and Clay Bavor discuss the new technology and the competitive AI landscape

October 11, 2024

20VC: with Bret Taylor

Bret Taylor, co-founder of Sierra, joins 20VC to talk about the biggest misconceptions in AI and how his startup, Sierra, is revolutionizing customer support.

October 2, 2024

No Priors: with Bret Taylor

Bret Taylor, co-founder and CEO of Sierra discusses building company-branded AI agents with unique personalities, goals, and guardrails and their potential to revolutionize customer support.

September 19, 2024

Invest Like the Best: with Bret Taylor

Sierra co-founder, Bret Taylor, joins "Invest like the Best" to discuss a strategic approach to AI integration, the different categories of agents and their scopes, and the essentials of craftsmanship.

September 3, 2024

Training Data: with Clay Bavor

Sierra is enabling companies to deploy AI agents that can handle complex customer interactions at scale. In this episode, Sierra's co-founder, Clay Bavor, describes how companies can create AI agents that represent the business.

August 27, 2024

Masters of Scale: with Bret Taylor

Sierra co-founder, Bret Taylor, joins Reid Hoffman to talk about OpenAI's world-shaping mission, why he founded Sierra and got back in the start-up game, and how business leaders should be using AI now.

August 8, 2024

Washington Post: The Futurist

Sierra co-founder Bret Taylor joins Washington Post Live to discuss how businesses could benefit from AI and manage the risks around the technology

June 25, 2024

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