Rails/Win-back week

Win-back week

Quiet/churned list on ClickUp. Five–ten draft win-backs. You send.

ClickUp · Resend

Paste into your agent. One block. The week is in the paste.

  • Quiet/churned rows on ClickUp; five–ten drafts this week
  • ClickUp holds the win-back list
  • Resend (or Email) holds gated drafts — you send
  • Thursday optional: one Tally feedback form
  • Friday: send-approval pack + one learnings line — no invented churn %

The rail

  1. Step 1Productivity
    Open the win-back list — ClickUp
    One ClickUp list for quiet/churned people. Free Forever. No second Space.

    Open ClickUp

    Win-back list

    Win-back week — Step 1 ClickUp

    Open one ClickUp list named for this win-back week. Output: empty list ready for quiet/churned rows. Do not invent a second Space. Do not invent churn rates or segment sizes. Sign up: https://clickup.com/signup Free Forever. No card required.

  2. Step 2Productivity
    Pull the segment into rows — ClickUp
    One row per person they named. Status they named. No fake churn %.

    Open ClickUp

    Quiet / churned rows

    Win-back week — Step 2 Segment

    Put quiet/churned people on the list. Only names, emails, and statuses they gave or that live in a list they pointed you at. Output: five–ten rows (name + status + owner if named). Mark which get drafts this week. Do not invent churn %, MRR lost, or reasons they left. Leave blanks. Do not send.

  3. Step 3Marketing
    Park five–ten win-back drafts — Resend
    Personalized drafts parked. Do not send without yes on each.

    Open Resend

    Gated drafts

    Win-back week — Step 3 Drafts

    Draft five–ten personalized win-backs for the marked rows. One offer line only if they named an offer. Output: drafts parked (subject + body + to). Status: draft — do not send. Prefer Resend for transactional-style win-backs. Email inbox is fine if that is where they send. Do not invent discounts, churn %, or proof. Soft slots (tone, offer, exclusions) come from their principal/memory — ask once if missing. Sign up: https://resend.com/signup Free: 3,000 emails/mo, 100/day. No card required for Free. Domain verify is still human. Agent never sends without an explicit yes on that message.

  4. Step 4Productivity
    Optional feedback form — Tally
    One short form if they want feedback. Share only when they say yes.

    Open Tally

    Why they left

    Win-back week — Step 4 Tally (optional)

    If they want a feedback form this week: build one short form (why quiet / what would bring them back). Output: form URL parked. Do not share publicly without yes. Do not email respondents without yes. Skip this step if they said no form. Sign up: https://tally.so/signup Free: unlimited forms and submissions (fair use). No card required for basics.

  5. Step 5Ops
    Friday approval pack — Friday recap
    Approval pack for drafts still gated. One learnings line. No invented churn %.
    Send pack + learnings

    Win-back week — Step 5 Friday

    Open the ClickUp list. List drafts ready for send (only those parked). Build a send-approval pack: who / subject / offer line used / status draft. Name one learnings line from what they told you or from form answers they asked you to read — never invent churn %. Output: Friday line. Do not send any win-back unless they said yes on that message. Optional: park a one-pager offer note in Notion only if they asked for a brief — Notion is not the list.

Paste the win-back week.

Nothing sends until you say yes. Drafts sit until you hit send.

Related tools

Win-back week · Skillrails