Podcasts

Showing 26 results

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.

10 March 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.

19 February 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.

29 January 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.

28 January 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.

14 January 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.

13 November 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."

23 October 2025

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.

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

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