Systems Lab

Agent skill

reengagement-segmenter

Segment a lapsed audience by the actual blocker that stalled each relationship, then plan a distinct reengagement motion per segment, including the segment that should be left alone.

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Filed under Outbound email.

From esmefong/gtm-skills · 8 skills · 0 · pushed 2026-09-04

What it does when it runs

Segment a lapsed audience by the actual blocker that stalled each relationship, then plan a distinct reengagement motion per segment, including the segment that should be left alone. Works on dormant pipeline, lapsed customers, cold trial users, or an inactive list. Applies a blocker taxonomy (never activated, timing, lost to incumbent, price, trust damage, drifted, unknown), enforces hard exclusions first (unsubscribed, complaints, active competitor contracts), flags records whose stated reason contradicts their evidence, and drafts sequences through the outbound-engine gate. Use whenever the user says "win-back", "reengagement", "re-engage", "lapsed customers", "dormant accounts", "stalled deals", "gone quiet", "cold pipeline", "churned users", or wants to revive a list without blasting it. Consumes icp-research and brand-voice-guide; sequences inherit outbound-engine's no-send discipline.

Read from the skill and the 9 files bundled beside it. A skill’s own description is written to be selected by an agent, so it describes the job and not the dependencies.

Keys and connectors you must supply
None found.
Hosts it reaches
  • www.techtimes.com
Tool permissions it declares
No allowed-tools in the frontmatter. It does act, so it runs under whatever permissions your session already grants.
Actions present in the files
writes files

Ask about reengagement-segmenter

Opens your assistant with this page's verified links already in the prompt.

Is this safe to install?ClaudeChatGPT
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Rather ask a human? Talk to Cheetah
git clone --depth 1 --filter=blob:none --sparse https://github.com/esmefong/gtm-skills.git /tmp/gtm-skills
git -C /tmp/gtm-skills sparse-checkout set "reengagement-segmenter"
mkdir -p ~/.claude/skills/reengagement-segmenter
cp -R "/tmp/gtm-skills/reengagement-segmenter/." ~/.claude/skills/reengagement-segmenter/

Picked up without a restart. A project skill of the same name is shadowed by your personal one. For one repository only, swap ~/.claude/skills for .claude/skills. Claude Code docs ↗

The folder is the same in every client that implements the format — 46 of them — so if yours is not above, only the destination changes.

Reproduced in full from esmefong/gtm-skills/blob/99400e67cdf7535d05377d7ca279ff81d550525e/reengagement-segmenter/SKILL.md, which is licensed MIT (repository). 832 words, 11 headings.

Reengagement Segmenter

Turn "the lapsed list" into distinct audiences with distinct reasons for silence, and treat the reason as the segment. The design rests on one argument: win-back blasts fail because they treat silence as one condition, when silence is the least informative signal a contact can send. A deal stalled at security review, a user who never reached value, and a buyer who signed with the incumbent all look identical in a recency report and need three different messages, or none.

The other half of the argument is the repo's standing one: the most valuable output of a reengagement pass is often the list of people you decide not to contact, documented.

What this consumes

InputFromWhat it provides
The lapsed recordsCRM export, deal notes, product events, support historyThe evidence each blocker call rests on
ICPicp-researchDisqualifiers (bad-fit lapse is leave-alone, not win-back), triggers for the why-now
Voice directorybrand-voice-guideThe register sequences are written in
What changed on your sideThe userReengagement needs a why-now; "we miss you" is not one

The last row is the load-bearing one. A reengagement sequence exists because something changed: your product closed the gap that stalled them, their situation visibly shifted, or a trigger from the ICP fired. No change, no sequence; that cohort waits.

The workflow

Five phases. Show the user the segment map (end of Phase 3) before any drafting.

Phase 1: Assemble the evidence, not just the list

Pull the lapsed records with whatever evidence exists per record: last meaningful activity, lifecycle stage reached, stated reasons (closed-lost fields, cancellation surveys), and observed behavior (support tickets, usage before silence, emails). First-party evidence is messy and contradictory; that is expected and handled in Phase 3, not smoothed over.

Phase 2: Run the exclusions first

Before any blocker reasoning, apply the hard gates from references/blocker-taxonomy.md: unsubscribed or do-not-contact, complaint history, active competitor contracts, ICP disqualifiers, and the dormancy horizon. These records go to the leave-alone lane with reasons, which ships in the deliverable. Reengaging someone who opted out is not a growth motion, it is a compliance incident.

Phase 3: Assign blockers, honestly

Tag each surviving record with a blocker from the taxonomy, citing the evidence. Three rules:

  • The evidence outranks the label. When the CRM says "price" but the thread shows a security stall, the record is flagged as a conflict and resolved by judgment, with the resolution written down. scripts/segment_audience.py detects these conflicts mechanically.
  • Unknown stays unknown. A record with no blocker evidence goes to the diagnostic segment, whose sequence asks one honest question instead of assuming a reason.
  • The script does the bookkeeping. Deterministic rules (exclusions, recency bands, tag precedence, conflict detection) run mechanically; the judgment calls are yours and get recorded.

Phase 4: Plan one motion per segment

Each blocker has its own sequence archetype in the taxonomy: the never-activated get the value they missed, the timing-stalled get a low-pressure trigger watch, the security-stalled get the specific thing that changed, the diagnostic segment gets one question. Two universal rules: reengagement sequences are shorter than cold ones (two to three touches), and every sequence opens with the why-now change, not with an apology for the silence.

Phase 5: Draft, gate, package

Draft in the brand voice and run every sequence through outbound-engine's sequence_gate.py: the freshness check applies to the why-now change, the slop list catches "just checking in" (the canonical reengagement failure), and the voice Avoid list holds. Package per references/output-template.md: the segment map with counts, the per-segment plans, the conflict log, and the leave-alone lane with reasons.

Scripts

ScriptWhat it doesNetworkKeys
scripts/segment_audience.pyDeterministic segmentation: exclusions, recency bands, blocker tags, conflict flags, countsNoneNone

Failure modes to avoid (the quality bar)

  • One blast to the whole list. The disease this skill treats.
  • "Just checking in." The outbound gate catches it mechanically; do not write it.
  • Guessing the blocker. No evidence means the diagnostic segment, not your best story.
  • Reengaging the excluded. Unsubscribes and complaints are permanent exits from this motion.
  • Apologizing for the silence. Open with what changed, not with the gap.
  • A hidden leave-alone lane. The records you chose not to contact, with reasons, are output.
  • Trusting the CRM label over the thread. Stated reasons are hypotheses; conflicts get logged.

Bundled references

  • references/blocker-taxonomy.md: the segments, the evidence each requires, the exclusion gates, and the sequence archetype per segment. Read at Phases 2-4.
  • references/output-template.md: the audience.json schema the script consumes and the segment report format. Read at Phases 3-5.
  • examples/cohere/: a dormant-pipeline pass in Cohere's voice on synthetic records (fictional counterparties, labeled, with real contradictions), the segment map, and a gated sequence for the security-stall segment.

Files bundled with it

These load only when the skill asks for them, so they cost nothing until it runs.

Need help setting it up?

This page tells you what reengagement-segmenter does and what it needs. Cheetah builds the agent setup it runs inside: data, CRM, sequencing and the guardrails.

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