Weekly Circle re-engagement email drafts in Gmail

Every Monday at 9am in my local time, sweep my Circle community for at-risk members and draft a personal re-engagement email to each one in Gmail. Do not send anything. Drafts only. I will review and send them by hand.

Trigger: cron, weekly on Mondays at 9am.

Step 1. Pull all current community members from Circle using List Community Members, paginating with per_page=100 until has_next_page is false.

Step 2. Filter to at-risk members. An at-risk member is someone who is still subscribed, joined the community more than 14 days ago, and has not posted, commented, or RSVPed to an event in roughly the last 21 to 30 days. Skip anyone who joined in the last 14 days because they are too new to call lapsed. If a member's last activity timestamp is not directly available on the member record, use Circle Advanced Search scoped to that member to find their most recent post, comment, or event RSVP and use that date.

Step 3. For each at-risk member, call Get Community Member to pull their full profile, including tags, segment, and any role or interest profile fields. Keep the member id, name, email, last-active date, last post or comment topic if available, the space they were most active in, and their tags or interests.

Step 4. For each at-risk member, find two or three recent high-engagement posts or upcoming events from the spaces that match their tags or interests. Use Circle Advanced Search or List Posts scoped to the relevant spaces, look at posts from the last 14 days, and pick the ones with the highest comment or like counts. If there is an upcoming event in one of their spaces, prefer that. Capture a short title and the link for each.

Step 5. Before drafting anything, dedupe against recent outreach. Call Gmail List Drafts with a query like subject:"[Circle re-engagement]" and look at any drafts from the last 60 days. Skip any member whose email already appears as the recipient of a re-engagement draft in that window, so we do not pester the same people week after week.

Step 6. Cap the run at 25 drafts so the community manager can actually review them. If the at-risk list is longer than 25 after the dedupe, prioritize members who used to be the most active (highest historical post or comment count) so we re-engage the people who mattered most first.

Step 7. For each member that survives the cap, call Gmail Create a Draft. The draft should be from me to that member's email. Subject line starts with the prefix [Circle re-engagement] (the dedupe in step 5 depends on this prefix) followed by a short, warm, personal subject, for example: [Circle re-engagement] Miss seeing you in the Founders space, Sara. The body should be short and warm, 3 to 5 short paragraphs, no marketing tone:

- Open by first name.

- Reference something specific about why we miss them: the topic of their last post, the space they used to be active in, or their role or tag. Not a generic 'we miss you' line.

- Link the two or three recent posts or the upcoming event from step 4, with one short sentence on why each is worth coming back for, tied to their interests.

- Close with a low-pressure invitation to jump back in, signed from me.

Step 8. At the end of the run, give me a short summary: how many members were swept, how many were flagged at-risk, how many were skipped because of recent re-engagement, and how many drafts ended up in Gmail. Include the names so I can scan it.

Important: never send any of the emails. Drafts only. The output of this workflow is a tidy stack of Gmail drafts I open in Gmail and send by hand.

Additional information

What does this prompt do?

Sweeps your Circle community every Monday morning to find members who have gone quiet but are still subscribed.
Looks up each at-risk member's tags, segment, and interests, then finds two or three recent posts or upcoming events they would actually care about.
Drafts a short, warm, personal re-engagement email per member in Gmail, opening by name and referencing something specific about why you miss them.
Caps the run at 25 drafts and skips anyone you already reached out to in the last 60 days, so your inbox stays reviewable and members are not pestered.

What do I need to use this?

A Circle community on the Business plan or above, with admin access.
A Gmail account you want the drafts created in.
A rough idea of how you define an at-risk member (the default is no posts, comments, or RSVPs in the last 21 to 30 days, and joined more than 14 days ago).

How can I customize it?

Shift the schedule (for example, every other Monday or every Friday afternoon) or the time of day.
Tighten or loosen the inactivity window, the new-member grace period, or the per-run draft cap.
Change the tone, subject line prefix, or signature so the drafts sound exactly like your community manager.
Narrow the sweep to one space group, one membership tier, or members carrying a specific tag.

Frequently asked questions

Will it send the emails automatically?

No. It only creates Gmail drafts. You open Gmail, skim each one, tweak anything that feels off, and hit send. Nothing leaves your account without your click.

How does it decide who counts as at-risk?

By default, members who are still subscribed but have not posted, commented, or RSVPed in roughly the last 21 to 30 days, excluding anyone who joined in the last 14 days. You can tune that window when you set it up.

Will the same member keep getting re-engagement emails every week?

No. Before drafting, the workflow checks your Gmail drafts for a re-engagement message to that member in the last 60 days and skips them if one already exists, so people are not pestered.

Will the emails actually feel personal?

Yes. Each draft opens by name and references something specific to that member, like the topic of their last post, the space they used to hang out in, or a recent post or event tied to their interests. It is not a generic 'we miss you' blast.

What if my community is huge and there are hundreds of inactive members?

The workflow caps each run at 25 drafts so you can actually review them. Anyone who is not drafted this week will resurface in a later run once you have worked through the current batch.

Do I need a paid Circle plan?

Yes. Circle's API is only available on the Business plan or above. If you are on a lower tier, you would need to upgrade before this works.