Christopher O’Donnell, Founder and CEO of Day.ai and former Chief Product Officer at HubSpot, joins CJ Gustafson and Kyle Poyar to explore what it takes to build an AI-native CRM from first principles in a moment when product development has “no rules.” He reflects on shifting from leading massive teams to coding daily, why CRM needs to return to serving CEOs rather than being trapped in operational bottlenecks, and how blending familiar interfaces with powerful AI assistants can reset user expectations. O’Donnell digs into market selection, product-market fit in rapidly evolving categories, agent-based pricing, and the cultural advantage of staying close to customers rather than the industry echo chamber, all while sharing candid stories about creativity, ecosystems, and the accelerating pace of AI-driven product craftsmanship.

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LINKS:

Day.ai: https://day.ai/

Christopher on LinkedIn: https://www.linkedin.com/in/markitecht/

Mostly Metrics: https://www.mostlymetrics.com

CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/

Growth Unhinged: https://www.growthunhinged.com/

Kyle on LinkedIn: https://www.linkedin.com/in/kyle-poyar/

Slacker Stuff: https://www.slackerstuff.com/

Ben on LinkedIn: https://www.linkedin.com/in/slackerstuff/

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Building AI-Native Software With No Rules | Christopher O’Donnell

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Building AI-Native Software With No Rules | Christopher O’Donnell