Your 2027 Retention Strategy Should Already Be Underway

Your 2027 Retention Strategy Should Already Be Underway

If your 2027 retention strategy starts in January, you’ve already lost time.

Every January, gyms fill with people saying the same thing, "New year, new me!" They assess where they are, decide where they want to be, set goals, build a plan, and start working toward better results. Businesses go through a similar exercise. New goals are announced, budgets change, priorities shift, and technology investments are reconsidered.

For Customer Success teams, those conversations should not come as a surprise.

The customers who may become your “unexpected” Q1 churn are probably giving you signals today. Adoption may have slowed, a champion may have left, support frustrations may be accumulating, business priorities may have changed, or the customer may simply have stopped seeing the value they expected when they purchased.

That is why I keep coming back to an approach I created and used earlier in my ecommerce career called BizFit.

BizFit was a structured business assessment designed to look beyond whether a customer was simply using our technology. We assessed the customer’s business, discussed goals, identified areas that could improve, and looked at how their existing technology could better support those goals.

In many ways, the CSM became the personal trainer.

A good personal trainer does not start by selling everyone the biggest membership package. They assess where the person is today, understand what they want to accomplish, develop the right plan, monitor progress, adjust when something is not working, and keep them motivated.

BizFit should work the same way.

Sometimes an assessment uncovers an opportunity for an additional product or service that can genuinely help the customer. That is good for the customer and can create expansion revenue for the company.

But sometimes getting the customer into the right fit means recommending less.

A customer may be paying for capabilities they no longer need. A downgrade might reduce short-term revenue, but it can also remove the frustration of paying for something that is not delivering value. Keeping a customer in an oversized solution simply to protect current ARR can make the eventual cancellation easier to justify. Getting them into the right fit can preserve the relationship, renewal, and opportunity to grow together later.

Other customers may not need to buy or remove anything at all. They may simply need more knowledge.

Maybe they need help understanding a feature they already own. Maybe they need training on a workflow that could save their team time. Maybe their reporting contains valuable information, but nobody has shown them how to read it and use it to make better internal decisions. Sometimes Customer Success creates value by helping customers get more from what they already have.

That still matters to retention.

Heading into 2027, CSMs should be asking:
-What does this customer want to accomplish next year?
-Are they getting the results they expected?
-What is preventing progress?
-Has their business changed?
-Are they in the right product or service configuration?
-Are they using the capabilities that matter?
-Do they understand the information their technology is already giving them?

AI can help surface changes in usage, recurring support issues, sentiment, product opportunities, meeting history, and other signals across a portfolio, but AI is not the personal trainer.

The CSM is.

AI can provide measurements and help identify patterns. The CSM talks with the customer, researches the account, understands the business context, asks the questions, and recommends the right next step. Sometimes that means expansion. Sometimes it means a downgrade. Sometimes it means education, training, or simply helping the customer make better decisions.

That is the difference between renewal management and retention management.

Renewal management asks whether the customer will sign another contract. Retention management asks whether the relationship is still the right fit and whether we are giving the customer enough reason to continue it.

Customer Success teams still have time before 2027 to identify risks, reset goals, improve adoption, right-size accounts, and strengthen relationships before renewal conversations become rescue missions.

Your customers are already thinking about next year, maybe it is time to get them BizFit.