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Podcast

Episodes of the Chief Customer Officer Podcast

Podcast

Are You a Sitting Duck or a Fortress?

Mar 12, 2026

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9 min read

Are You a Sitting Duck or a Fortress?

how complex is the solution for the customer to adopt, and how hard is it to replicate?

Podcast

Cut Your Own Prices Before Someone Else Does

Mar 5, 2026

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10 min read

Cut Your Own Prices Before Someone Else Does

How AI is changing the landscape on traditional SaaS products

Podcast

The Wisest Person in Your Company You're Not Talking To

Feb 26, 2026

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9 min read

The Wisest Person in Your Company You're Not Talking To

Jon argues that the law department's job isn't to say no — it's to pave the road so the business can move fast.

Podcast

What we're building today w/ AI

Feb 19, 2026

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7 min read

What we're building today w/ AI

Just a real conversation about what they've each been building with Claude Code and Claude Cowork over the past few weeks, and what it's revealing about the future of software, teams, and CS.

Podcast

AI Predictive Customer Success w/ Justin Chappell

Feb 5, 2026

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4 min read

AI Predictive Customer Success w/ Justin Chappell

Justin Chappell breaks down the shift from proactive to predictive CS, how OneTrust cut onboarding from 44 days to 8, and the four new roles every AI-first CX team needs.

Podcast

Consensus on GRR, none on Customer Success

Jan 29, 2026

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4 min read

Consensus on GRR, none on Customer Success

CS teams are a mess of three-way splits—where they report, how they're paid, where they sit on the P&L. We break down the data and argue for a clearer path.

Podcast

Context is King

Jan 22, 2026

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32 min read

Context is King

AI agents are only as good as the context they have. We break down why enterprise software becomes more valuable—not less—and where deterministic workflows still beat AI.

Podcast

Death of the Coverage Model

Jan 15, 2026

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4 min read

Death of the Coverage Model

The coverage-based CSM model is dying—and now predictive, signal-driven customer success will replace it.

Podcast

Agentic Renewals

Jan 8, 2026

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47 min read

Agentic Renewals

We break down how to actually build AI agents for your renewal process—not theory, but the specific agents you'd deploy, what platforms to use, and where most teams get stuck.

See you in your inbox this Sunday

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