EPISODE · Sep 12, 2025 · 1H 8M
EP 150: Bret Taylor (CEO, Sierra): A New Class of Software Winners
Bret Taylor is the CEO of Sierra and Chairman of the Board of OpenAI. He previously served as co-CEO of Salesforce. I sat down with Bret to explore how the AI revolution compares to previous platform shifts and what it means for both startups and incumbents navigating this transition. (00:00) Introduction and Recent Milestone (00:38) AI Market and Historical Comparisons (02:30) Competitive Landscape and Business Models (06:02) Outcome-Based Pricing and Value Creation (13:52) Technological Shifts and Business Transitions (26:32) Adoption Challenges and Forward Deployed Engineering (37:21) Early Investment in Snowflake and Cloud Strategy (38:02) Enterprise Software Market Dynamics (38:38) AI Agents and Implementation Costs (41:06) Democratization of Software Development (43:35) The Future of Software Companies and AI Agents (49:36) Consumer Behavior and AI Agents (58:56) The Role of AI in Customer Experience (01:01:25) Career Advice in the Age of AI Executive Producer: Rashad Assir Mixing and editing: Justin Hrabovsky Check out Unsupervised Learning, Redpoint's AI Podcast: https://www.youtube.com/@UCUl-s_Vp-Kkk_XVyDylNwLA 🎙 Listen to the show Apple Podcasts: https://podcasts.apple.com/us/podcast/the-logan-bartlett-show/id1606770839 Spotify: https://open.spotify.com/show/5WqBqDb4br3LlyVrdqOYYb?si=3076e6c1b5c94d63&nd=1 🎥 Subscribe on YouTube: https://www.youtube.com/channel/UCugS0jD5IAdoqzjaNYzns7w?sub_confirmation=1 Follow on Socials 📸 Instagram - https://www.instagram.com/theloganbartlettshow 🐦 Twitter - https://twitter.com/loganbartshow 🎬 Clips on TikTok - https://www.tiktok.com/@theloganbartlettshow About the Show Logan Bartlett is a Software Investor at Redpoint Ventures - a Silicon Valley-based VC with $6B AUM and investments in Snowflake, DraftKings, Twilio, and Netflix. In each episode, Logan goes behind the scenes with world-class entrepreneurs and investors. If you're interested in the real inside baseball of tech, entrepreneurship, and start-up investing, tune in every Friday for new episodes.
What this episode covers
Bret Taylor is the CEO of Sierra and Chairman of the Board of OpenAI. He previously served as co-CEO of Salesforce. I sat down with Bret to explore how the AI revolution compares to previous platform shifts and what it means for both startups and incumbents navigating this transition. (00:00) Introduction and Recent Milestone (00:38) AI Market and Historical Comparisons (02:30) Competitive Landscape and Business Models (06:02) Outcome-Based Pricing and Value Creation (13:52) Technological Shifts and Business Transitions (26:32) Adoption Challenges and Forward Deployed Engineering (37:21) Early Investment in Snowflake and Cloud Strategy (38:02) Enterprise Software Market Dynamics (38:38) AI Agents and Implementation Costs (41:06) Democratization of Software Development (43:35) The Future of Software Companies and AI Agents (49:36) Consumer Behavior and AI Agents (58:56) The Role of AI in Customer Experience (01:01:25) Career Advice in the Age of AI Executive Producer: Rashad Assir Mixing and editing: Justin Hrabovsky Check out Unsupervised Learning, Redpoint's AI Podcast: https://www.youtube.com/@UCUl-s_Vp-Kkk_XVyDylNwLA 🎙 Listen to the show Apple Podcasts: https://podcasts.apple.com/us/podcast/the-logan-bartlett-show/id1606770839 Spotify: https://open.spotify.com/show/5WqBqDb4br3LlyVrdqOYYb?si=3076e6c1b5c94d63&nd=1 🎥 Subscribe on YouTube: https://www.youtube.com/channel/UCugS0jD5IAdoqzjaNYzns7w?sub_confirmation=1 Follow on Socials 📸 Instagram - https://www.instagram.com/theloganbartlettshow 🐦 Twitter - https://twitter.com/loganbartshow 🎬 Clips on TikTok - https://www.tiktok.com/@theloganbartlettshow About the Show Logan Bartlett is a Software Investor at Redpoint Ventures - a Silicon Valley-based VC with $6B AUM and investments in Snowflake, DraftKings, Twilio, and Netflix. In each episode, Logan goes behind the scenes with world-class entrepreneurs and investors. If you're interested in the real inside baseball of tech, entrepreneurship, and start-up investing, tune in every Friday for new episodes.
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EP 150: Bret Taylor (CEO, Sierra): A New Class of Software Winners
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