Podcasts

Sierra CEO Bret Taylor on Agents, Loyalty, and Distribution

Wil Slickers sits down with Skift Head of Research Seth Borko to break down what matters most from the Skift Global Forum conversation with Sierra CEO Bret Taylor.

April 13, 2026

Thought leadership

Bret Taylor at Remarkable Retail podcast

Is AI Retail's New Front Door?

Steve Dennis sits down with Bret Taylor, Chairman of OpenAI and CEO and co-founder of Sierra. Taylor outlines how AI agents are emerging as the new “digital front door” for retail, unifying customer interactions into a single intelligent interface.

March 31, 2026

Thought leadership

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

How Sierra Is Pulling Ahead in the AI Race

Bret Taylor explains why “competitive intensity” is a core value at Sierra, and why he believes AI won’t lead to a world where people stop working.

March 9, 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

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