Weekly Circle re-engagement 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.