Insights

Points of view on CS,
GTM, and AI in practice

Practical frameworks and hard-won perspective from 30 years inside B2B SaaS post-sale organizations.

What PE-Backed CS Actually Looks Like
Series 2  ·  New

Written for PE-backed CEOs and operating partners. The central argument: stable GRR is not the same as healthy CS — and the difference shows up at the worst possible time.

Coming Next

Posts 7–8 publish over the coming weeks — what good looks like at $25M vs. $75M ARR, and how to tell if your CS is exit-ready. Follow on LinkedIn to catch each post as it publishes.

The New Customer Success
Series 1  ·  8 Posts  ·  Complete

Written for CS practitioners — leaders and CSMs who run the function. What the role demands now, why most CS organizations aren’t built for it, and what to do about it.

Pinned Resource
The Outcome-Based CS Framework
Five pillars. A maturity model. A conviction that measurable customer outcomes are the product — not a metric. The complete framework for building a post-sale org that drives growth.
View the Framework →
PE-Backed SaaS · CS Leadership · Revenue Retention

What “We Have a CS Team” Actually Means

Having the function isn’t the same as having the model. Here’s the one question that separates a relationship-oriented CS team from an outcome-oriented one — and why it matters before the divergence shows up in your numbers.

6 min read
PE-Backed SaaS · CS Leadership · Revenue Retention

The Difference Between a CS Team That Retains and One That Defends

Reactive CS and proactive CS can produce identical GRR numbers for 18 months. Then they don’t. Here’s what each model looks like from the CEO’s chair.

6 min read
PE-Backed SaaS · Operating Partners · Portfolio Governance

What Your Operating Partner Isn’t Asking, But Should Be

PE boards watch GRR and NRR. Almost none of them ask how those numbers are being held. That gap is where risk hides — and where the exit story gets complicated.

6 min read
PE-Backed SaaS · Revenue Retention · CS Strategy

The First Discount Isn’t the Trap

GRR improved by 20 points and the board celebrated. Nobody asked how they got there. What purchased inertia actually costs — on one account, over two years.

7 min read
PE-Backed SaaS · Revenue Retention

Your GRR Went Up. That’s Not the Whole Story.

GRR went from 65% to 85% and everyone exhaled. But stable metrics can mask a broken model. The fix that moves the number isn’t always the fix that builds the business.

6 min read
Customer Success Strategy

The Sr. CSM Job Description I’d Write Today (and Why It Looks Nothing Like 2019)

For twenty years I opened every CSM JD the same way. The philosophy was right. Everything underneath it wasn’t.

2 min read
Customer Success Strategy

You Haven’t Built a Customer Success Function. You’ve Built a Junior Sales Team.

Most CS organizations are caught between two wrong models. Both are wrong. Both fail. Here’s what the right model actually looks like.

9 min read
Customer Success Strategy

Expansion Without Selling: How Great CSMs Grow Accounts Without Acting Like Sales Reps

When CS leaders push their teams toward commercial conversations, they lose the one thing that actually drives revenue. Trust.

9 min read
CS Leadership & AI Enablement

Your CSMs Are Using AI. That Doesn’t Mean They’re Doing the Job.

The outputs have never looked better. The judgment gaps have never been harder to see. What AI actually changed about CS — and what it exposed.

8 min read
Customer Success Strategy

Green Doesn’t Mean Healthy. It Means Active.

We built Customer Success around the wrong definition of success. The three-link chain — business pain, solution value, outcomes achieved — is how we fix it.

8 min read
Customer Success Strategy

The Four Layers of Business Intelligence Every CSM Needs

Usage data tells you what happened. Business intelligence tells you what matters. The framework that separates strategic partners from account babysitters.

8 min read
Customer Success Strategy

Your CSM Should Be More Like Your Doctor

Even today’s overworked PCP has disciplines most CSMs don’t. A framework for proactive customer health monitoring — and how AI makes it possible at scale.

5 min read
Customer Success Strategy

The “I’m Your Advocate” Era Is Over

Advocacy is reactive by nature. The CSMs delivering real retention and expansion aren’t advocates — they’re strategic partners.

5 min read