The Expansion Playbook Newsletter

Weekly frameworks to help expand your customers, company, and career. Read by 500+ CS & Sales leaders.

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Past Issues

Name the Win

You can deliver $3 million of value and still lose the renewal, because value the customer never observed gets absorbed into everything else that happened that year. Name the Win is the discipline of calling your shot before the work starts, stating the result back the week the number moves, and repeating it continuously so the renewal becomes a harvest instead of a scramble. A result the customer cannot see is a result that did not happen.

July 8, 2026Read →

Know Why You Miss

A streaky shooter chalks up an off night to bad luck. An expert knows why every miss happened, so every miss becomes a correction they can make mid-game. Customer success is the same game: define the fundamentals of a make, diagnose which one is missing, and fix it on the next shot instead of explaining the loss at renewal.

June 29, 2026Read →

Two Sides of the Same Coin

Most teams run two motions: a customer success team watching a health score for risk, and an expansion team chasing more revenue. But risk and expansion share one core. Define what success looks like for one outcome in four parts, technical, behavioral, outcome, and time, and the same measurement, the Dual Signal, tells you both stories. All four met means the customer is ready to grow. Any one missing means they are at risk before the lagging numbers ever turn red. And there is really no such thing as retention.

June 25, 2026Read →

The Outcome Lie

Building the tool was never the win. Hitting the usage metrics was never the win. The only thing that counts is whether the outcome actually changed, and almost nobody is checking. The Outcome Lie is accepting a proxy as proof, and it costs you with your customers and inside your own company.

June 17, 2026Read →

Success Stories, Not Case Studies

Most teams treat a success story like a peer-reviewed case study: baseline the workflow for a quarter, get legal sign-off, publish a year later. The biggest customer wins actually happen in the first two weeks. Lock the baseline early, catch the win in the moment, and ask permission while the customer is still glowing.

June 11, 2026Read →

The 67% Health Score Problem

A customer success team rolls out a 0-to-100 health score, and then a real account comes up at 67%. Nobody in the room can say whether that is good, bad, or what to do about it. The fix is to stop scoring risk on a continuum and replace the score with two binary lists of the things that actually predict whether a customer succeeds.

June 4, 2026Read →

Off by 5 Degrees

A plane that leaves Chicago for London five degrees off course lands in Frankfurt, 344 miles past its destination. The same thing happens to a customer success team when it celebrates a metric that has quietly drifted from the outcome. The wrong metric makes the operator look like they are winning while the customer is failing. Choosing the right metric is the expertise.

May 28, 2026Read →

The Driver's Seat

When you work with a customer, someone is always in the driver's seat. If it isn't you, it's the customer, and they'll steer you right back into the problem they hired you to solve. The Driver's Seat is the discipline of earning the right to lead through captured expertise, then defending it in the four moments that decide every customer relationship.

May 21, 2026Read →

Shape the Goal

Most customers don't walk in with a goal worth getting. They walk in with project tasks, vague aspirations, and whatever language the sales team handed them on the way out the door. The job isn't to ask for goals. It's to shape them.

May 14, 2026Read →

The No-Gap Mission

Most mission statements describe what the company does. The best ones describe what the customer is trying to accomplish, with the company as the path that gets them there. The No-Gap Mission is the difference between a sentence that talks past your customer and one they recognize as their own goal.

May 8, 2026Read →

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