Don't stop at the close: retain and expand

Before you wire anything, write down what a healthy customer looks like in your product. Pick three signals and no more. Good candidates are logins in the last 14 days, seats used against seats bought, and the date the contract renews.

Put them in one place. A HubSpot company record with three custom properties works well. So does a Google Sheets tab with one row per customer.

A signal only matters when it starts an action. Write every trigger as one line: when this happens, do that. These are the starting points I would use, and you should adjust them to your own data:

• Seat use above 80 percent for two weeks: draft a note offering more seats.
• No login for 14 days: draft a check-in that asks one question.
• Renewal in 90 days: draft a short brief for a renewal conversation.
• Feature adoption stalls after 30 days: send a how-to with one link.

Treat the numbers as guesses until your own accounts correct them. Review them after the first ten times a rule fires.

Connect the signals to an automation in Zapier or Make. When a rule fires, the flow sends the account facts to Claude with a short prompt. Say who the customer is, what fired, what they bought and what you want them to do next.

Claude drafts the message and the flow drops it into a Slack channel or your drafts folder. I would keep a human send step for anything that touches money. You read it, change a line and send it.

The cheapest retention work happens right after the sale. Set three touches: day 3 asks whether setup is clear, day 14 asks what has happened so far, and day 30 asks what result they have seen. Each one is a single question.

The answers are the earliest churn signal you will get. The day 30 answer is often your first expansion lead too. Log each reply on the account record.

Every Monday, spend 20 minutes on a list the machine builds: the accounts where a rule fired last week. Cap it at five. Anything beyond five waits for next week.

Write the action you took next to each account. This keeps your scarce hours on the conversations that move money, which is the same principle as in Build it this week: the action plan. The same follow-up logic from Follow-up as a system, not willpower applies here too.

Track net revenue retention once a quarter. Take the revenue from last quarter's customers, add their expansion, subtract churn and downgrades, and divide by where you started. New customers do not count. Above 100 percent means your existing base grows on its own.

The full method is in grow net revenue retention. For the deeper signal work, read build expansion signals into your motion and run customer success without a CS team. Once triggers fire reliably, upsell and cross-sell triggers run by AI agents shows how to hand more of the drafting to agents.

• Tracking ten signals, so none of them gets acted on.
• Letting AI send expansion emails without reading them first.
• Asking for an upsell before the customer has seen any value.
• Starting the renewal conversation only when the renewal date arrives.
• Reading a quiet customer as a happy one.
• Changing every rule at once, so you cannot tell which one worked. Find the one bottleneck and fix only that applies to this station as well.

• Every customer has a record with the three signals filled in.
• Your Monday list has five accounts or fewer, and each one has a note about what you did.
• At least one expansion or save conversation each month started from a rule, not from luck.
• Net revenue retention is visible every quarter and is moving in the right direction.
• You hear about a problem account from your dashboard before you hear it from the customer.