Customer Success Check-in

Most businesses only talk to customers when something is wrong or money is changing hands. That trains the customer to associate your name with friction. The Customer Success Check-in flips the pattern — every message has a real reason behind it, lands when there's something genuine to say, and gives before it asks.

The skill picks the check-in type before it writes a word. Value reinforcement when the data tells a story the customer hasn't noticed. Milestone celebration when there's an actual milestone — twelve months, a thousand tickets handled, a specific result worth naming. Value-add when you've found something useful and they're the obvious recipient. Re-engagement when usage has dropped and a heavy "we miss you" email would make it worse. Feedback request when a specific question will get a specific answer, not a generic survey link they'll ignore.

Every email runs the WARM structure: a specific reason for reaching out, something useful in the body, a light ask, and enough personalisation that the email could not have been sent to anyone else on the list. "Just checking in" is treated as a banned opener — if the skill can't find a trigger for the outreach, it tells you the email shouldn't be sent yet.

The output ships with a follow-up plan for three scenarios: they respond positively, they go silent for five days, or they surface a concern you didn't know about. That last branch matters most — proactive check-ins occasionally uncover problems, and you want a response ready before you find out. Internal notes log the date, type, and next scheduled touch so the cadence stays varied across the year rather than collapsing into a monthly autoresponder.

It refuses to disguise a sales pitch as a check-in. If the message is really an upsell, the skill names it and offers to route the request through a separate outreach pattern. A check-in that's really a pitch is the fastest way to make every future check-in feel transactional — and once that signal lands, it's hard to undo.