How AI Is Repricing Every Software Company

Vanta co-founder and CEO Christina Cacioppo returns to discuss what it takes to build an enduring software company in the age of AI. She and Patrick explore the “SaaSpocalypse,” why high-growth, high-margin software businesses are facing collapsing valuation multiples, and the dangers of charging customers for AI tokens. Christina shares how Vanta is reinventing its products around AI agents, why the talent wars have driven compensation for top employees up 10x, and what Silicon Valley is getting wrong about AI. They also discuss the future of cybersecurity, the extraordinary story behind Vanta's billion-dollar billboard war, and why rebuilding trust in technology may be the biggest opportunity of all. TIMESTAMPS 0:00 Intro 4:17 Surviving the SaaSpocalypse 9:40 The AI Pricing Trap 16:17 Rebuilding Software for AI 22:43 Silicon Valley's Talent Wars 31:57 What's Overhyped in AI 38:39 Security at Machine Speed 47:16 Reinventing Software 55:37 The Billboard War 60:38 Rebuilding Trust in Technology Presented by Ramp: https://ramp.com/invest Sponsored by Vanta, WorkOS, Rogo, and Ridgeline: https://www.vanta.com/invest https://workos.com/ https://rogo.ai/invest https://www.ridgelineapps.com/ ****** Patrick O'Shaughnessy is the CEO of Positive Sum. All opinions expressed by Patrick and podcast guests are solely their own and do not reflect the opinion of Positive Sum. This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions. Clients of Positive Sum may maintain positions in the securities discussed in this podcast. To learn more, visit psum.vc

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