Podcasts

Bret Taylor of Sierra on AI agents, outcome-based pricing, and the OpenAI board

Bret Taylor, co-founder of Sierra and Chair of the OpenAI board, joins John for a pint to discuss the rapid shift toward an agentic future.

March 10, 2026

Thought leadership

Bret Taylor on AI and the Future of Software

Jack Altman and Bret Taylor unpack the so-called “SaaS-pocalypse” and what AI agents mean for the future of enterprise software.

February 19, 2026

Thought leadership

Interview: Bret Taylor of Sierra and OpenAI

Andrew Palmer sits down with Bret Taylor, Chair of OpenAI and co-founder of Sierra, to discuss the future of AI agents and their impact on businesses around the world.

January 29, 2026

Thought leadership

Is AI Killing Software? With Bret Taylor

Bret Taylor, CEO of Sierra and chair of OpenAI's board, joins Big Technology Podcast to discuss how AI is reshaping software, from vibe coding to the rise of AI agents that will replace dashboards, forms, and the way we interact with technology.

January 28, 2026

Thought leadership

Bret Taylor (Sierra, OpenAI): Why the future of enterprise software belongs to vertical agents

Sierra founder and OpenAI board chairman Bret Taylor joins Pigment co-CEO Eléonore Crespo to discuss how AI agents are reshaping enterprise software and customer experience.

January 14, 2026

Thought leadership

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.

November 13, 2025

Thought leadership

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."

October 23, 2025

Thought leadership

Clay Bavor featured on the Heart of Healthcare podcast

The Heart of Healthcare 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.

October 20, 2025

Healthcare Thought leadership

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

Healthcare Thought leadership

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