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Past Articles

Every edition we’ve sent. Clear thinking on metrics, leadership, and running customer teams that actually work.
high output leaders 📈

high output leaders 📈

The way that executives can think about building the narrative of output and contribution

Podcast

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

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.

AI & Digital CS

solving AI's productivity problems

solving AI's productivity problems

7 key steps for using AI to reduce bottlenecks and increase productivity.

Podcast

What we're building today w/ AI

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.

Leadership

+1

the 2026 CCO org chart

the 2026 CCO org chart

The old blueprint is obsolete. Here is the new CCO org chart for the AI era.

Leadership

+1

take advantage of status quo

take advantage of status quo

Sales teams wake up every morning fighting the status quo. You should be using it to win.

Podcast

AI Predictive Customer Success w/ Justin Chappell

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

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.

AI & Digital CS

why point solutions are dying

why point solutions are dying

Core platforms will survive. But point solutions are about to suffer at the hands of AI.

Podcast

Context is King

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.

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