Leaving HubSpot to Start Day.ai

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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SPONSORS:

Metronome is real-time billing built for modern software companies. Metronome turns raw usage events into accurate invoices, gives customers bills they actually understand, and keeps finance, product, and engineering perfectly in sync. That’s why category-defining companies like OpenAI and Anthropic trust Metronome to power usage-based pricing and enterprise contracts at scale. Focus on your product — not your billing. Learn more and get started at https://www.metronome.com

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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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RELATED EPISODES:

OpenAI’s Impossible Math: $500B or Bust?

https://youtu.be/L6PLnvjcnpk

The Product-Market Fit Treadmill | Brian Balfour Explains

https://youtu.be/I5UqGlBOdoA

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TIMESTAMPS:

00:00:00 Preview and Intro

00:01:10 Sponsors – Metronome | Pulley

00:03:31 Introducing Christopher O’Donnell

00:05:20 From Music to Software

00:07:10 Leaving HubSpot to Start Again

00:09:00 Inspiring Teams at Scale

00:10:50 What It Means to Build AI-Native

00:12:40 How Location Shapes Careers

00:14:30 Relearning in an AI-First Era

00:16:20 Shipping and Iterating With AI

00:18:10 The App as the Main Character

00:20:00 Using AI to Pressure-Test Decisions

00:21:50 Rethinking CRM Expectations

00:23:40 Choosing a Hybrid CRM Approach

00:25:30 Entering a Massive Market

00:27:20 PMF in the AI Era

00:29:10 The CRM Status Quo and Its Defenders

00:31:00 How CRM Lost Its Purpose

00:32:50 Rethinking Seat-Based Pricing

00:34:40 Why Credit Models Confuse Buyers

00:36:30 Flat-Rate Plans and Ecosystem Dynamics

00:38:20 Enterprises Sitting on AI Commits

00:40:10 Conference Room Dystopia

00:42:00 Getting Burned by Ecosystems

00:43:50 Trying Amazon’s Rufus

00:45:40 Suno and the Music-Tech Debate

00:46:28 Show Outro

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