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Past Articles

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

Podcast

Are You a Sitting Duck or a Fortress?

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?

stop mapping the wrong journey

stop mapping the wrong journey

Most SaaS companies have built a detailed map of their internal operations and quietly convinced themselves it’s the same thing as a customer journey. It’s not.

Podcast

Cut Your Own Prices Before Someone Else Does

Cut Your Own Prices Before Someone Else Does

How AI is changing the landscape on traditional SaaS products

high output leaders 📈

high output leaders 📈

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

Leadership

What is a Chief Customer Officer

What is a Chief Customer Officer

The growing importance of a customer-focused business leadership role

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The old blueprint is obsolete.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.

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