Monthly Kit re-engagement pass on dormant subscribers
On the first Monday each month, find Kit subscribers who have gone quiet, sort save-worthy from cold, and draft a win-back email for you to review.
ConvertKit
SlackMarketingEmail AutomationResearch & MonitoringOn the first Monday of every month, run a re-engagement pass on my Kit (formerly ConvertKit) subscriber list. The goal is simple: stop paying for dead subscribers without accidentally cutting off people who are still warm. Never auto-unsubscribe anyone. This workflow only tags and drafts; a human sends.
Step 1. Page through my full Kit list with List Subscribers. For each subscriber, capture their id, email, created date, and current state. Use cursor pagination all the way through so nothing is missed on large lists.
Step 2. Build an engagement picture for each subscriber. Call List Broadcasts to pull my recent sends, then Get Broadcast Stats for the last roughly 10 to 15 broadcasts so I have open and click activity to reason over. Where useful, call List Tags for Subscriber on the questionable ones to see how they were originally segmented (lead magnet, course buyer, freebie, etc.). Combine those signals to decide who has not opened or clicked in about the last 90 days.
Step 3. Bucket the dormant subscribers into two groups. 'Worth saving' means they subscribed in the last 90 days (so they never really got a chance) or they previously engaged with a broadcast before going quiet (so they used to care). 'Cold' means long-dormant with no meaningful signal in the recent broadcast history. Do not act on the 'cold' bucket in this run beyond counting it; I will review that group by hand.
Step 4. Draft a short re-engagement broadcast tailored to the 'worth saving' cohort using Create Broadcast. Save it as a draft only, never scheduled, never sent. Keep the tone warm and low pressure: acknowledge it has been a while, remind them why they signed up, and give one concrete reason to stay. Do not fabricate numbers or promises. Pick a subject line that sounds like it came from me.
Step 5. Tag every 'worth saving' subscriber with 're-engage-YYYY-MM' (for example 're-engage-2026-07') using Tag Subscriber by ID, so at send time I can filter the draft's audience to exactly that cohort. If the tag does not exist yet, create it first. Do not tag the 'cold' bucket.
Step 6. Post a Slack summary with Send a Message to my chosen channel (default: #kit or my DM). Include: total subscribers scanned, dormant count, 'worth saving' count, 'cold' count, the exact re-engage tag applied, the draft subject line, and a reminder to open Kit to review and send. Keep it short and skimmable.
Guardrails: draft-only in Kit (never schedule, never send), tag-only for cohorting (never unsubscribe), and Slack is a notification, not an approval gate. If the list is huge, prioritize accuracy over speed and paginate patiently. If broadcast stats are unavailable for a period, note that in the Slack summary rather than guessing.
What does this prompt do?
- Scans your Kit list once a month and flags subscribers who have not opened or clicked in roughly 90 days.
- Splits the dormant list into 'worth saving' (recent signups or previously engaged) versus 'cold' (long-dormant) so you never blanket-blast people who are already gone.
- Drafts a short re-engagement email in Kit for the save-worthy group as a draft only, so you review and send when you are ready.
- Tags the same cohort with a dated re-engage tag so you can target the draft to exactly them at send time.
- Posts a Slack summary with the counts, the buckets, and the draft subject line before anything else happens.
What do I need to use this?
- A Kit (formerly ConvertKit) account connected, with an active subscriber list.
- At least a few months of past broadcasts in Kit so the agent has real open and click history to grade engagement against.
- A Slack workspace and a channel or DM where you want the monthly summary to land.
How can I customize it?
- Change the dormancy window from the default 90 days to whatever matches your send cadence.
- Route the Slack summary to a different channel or DM, or add a co-founder to the recipients.
- Tweak the draft's tone, subject line, or the framing of what counts as 'worth saving'.
FAQs
Will this unsubscribe anyone automatically?
What counts as a dormant subscriber?
How does it decide who is 'worth saving' versus 'cold'?
Will the re-engagement email be sent automatically?
Can I run this on Kit if my list has thousands of subscribers?
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Stop paying for dead Kit subscribers.
Set this up once and every month you will know exactly who to win back, with the draft already waiting for your review.