The Expansion Playbook Newsletter
Weekly frameworks to help expand your customers, company, and career.
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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.
There's No Such Thing as Saving a Customer
Most save plays don't save anybody. They buy one more contract and move the churn to the next renewal. Here is the one-cycle save, the save play with a near 100% save rate that churned worse at the next renewal than doing nothing, the three levers that work instead, and how DearDoc tripled its save rate.
Past Issues
There's No Such Thing as Saving a Customer
Most save plays don't save anybody. They buy one more contract and move the churn to the next renewal. Here is the one-cycle save, the save play with a near 100% save rate that churned worse at the next renewal than doing nothing, the three levers that work instead, and how DearDoc tripled its save rate.
The Feature Trap
When one feature decides whether a customer stays, the conversation started in the wrong place. Start with the product and every conversation becomes pass or fail. Start with the outcome and you have dozens of ways to move the number. Here is the Feature Trap, the SalesRabbit customer who should have gone live six weeks ago, and what a Customer Results Map shows when a customer gets stuck on one feature.
Everyone Gets Expansion Backwards
Most companies start with what they have to sell and go looking for customers to buy it. That is backwards. Expansion exists because customers have increasing needs, and the companies that last become everything to somebody, not something to everybody. Here is why market share taps out and wallet share doesn't, how to pair paid and non-paid expansion, why the line between upsell and cross-sell is the use case, and why expanding a customer gets you retention for free.
Renting Competence
Everyone thinks AI is the great equalizer. It is the great divider: it makes the people who understand how customers win dramatically more capable, and it leaves everyone else stunted, because a prompt hands you the output without the struggle that was supposed to make you good. That is renting competence. Here is what my fourth-grade math teacher knew, what I had to figure out the hard way at SalesRabbit, and the four moves of the struggle that turn AI into the thing that makes you faster instead of replaceable.
Getting More Resources Is a You Problem
I begged my CEO for two more CSMs for months and got nowhere, because I was walking in with the emotion of one bad call and handing him the job of deciding whether the need was real. Leaders are much better editors than they are creators. Here is the working premise that changed the answer, the five-input capacity model behind it, and the hire trigger that stops you hiring to catch up.
The Only ROI Conversation That Works
There are three ways to talk about value with a customer. The payback pitch before the deal, the retroactive case at renewal, and the one that starts with the number the customer has to hit whether you exist or not. Two of them are about you, and those are the two everyone uses the most. Here is the third one, and the four moves that make it work.
Creating Customer Leverage
A friend told his teenagers something that changed their grades overnight: you're not getting good grades for me, these are your grades. That is the exact thing we get wrong with customers. Almost every ask we make is framed around our own metrics, and the customer can tell. Here are the four moves that tie the ask to what they already told you they have to achieve.
Everything Has Changed and Nothing Has Changed
A contact of mine has spent a year inside a company acquired by OpenAI, and I assumed he had seen the cutting edge of AI-powered customer success. He got no insight, no guidance, and nothing more advanced than what his team already had. I have now looked under the hood at several AI companies, and they all have the same problems we have been working on for 20 years. You are not behind. Nobody is ahead.
Know Your Customer's Business Better Than They Do
An onboarding specialist told me her customer had eight years more education than she did and had practiced medicine for twenty years, so who was she to tell them how to run their business. The answer is that you will never out-know them, and you do not have to. You have to out-model them on the two to five numbers that decide whether they make money, and that takes weeks of focused effort rather than a career.
Stop Waiting for Permission
A business law professor refused to give our class a rubric. Answer the question, he said, and that was the entire assignment. It turned out the arbitrary requirements were never the work, they were the packaging around the work. Most of the limits on your job are the same: rubrics you wrote for yourself, and they are standing between you and the outcome you are actually being judged on.
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