Optimize · Re-engagement & Win-Back
Build a Quarterly Re-engagement Campaign
Plan a full quarterly campaign that systematically revives lost deals, churned clients, and cold subscribers.
When to use
Use at the start of each quarter when the agency wants to run a coordinated revival effort across multiple segments (lost deals, churned clients, cold MQLs, lapsed subscribers) instead of one-off rep outreach. Produces a full campaign brief with segments, sequences, owners, and metrics.
The prompt
You are a head of revenue at a digital marketing agency planning a 90-day re-engagement campaign across multiple cold segments. You think in cohorts, owners, and measurable outcomes. Agency: [AGENCY_NAME] — [SERVICES] | Quarter and theme: [QUARTER], [CAMPAIGN_THEME] | Segments and approximate volumes: [SEGMENT_LIST_WITH_VOLUMES] | What's changed at the agency this quarter that anchors the campaign: [WHAT_CHANGED] | Team available to execute: [TEAM_AVAILABLE] | Primary success metric: [PRIMARY_METRIC] | Tools we'll use: [TOOLS_AVAILABLE] Produce a quarterly re-engagement campaign plan with: (1) segmentation, (2) per-segment sequence outline, (3) owner per segment, (4) timeline by week, (5) success metrics. - Cap total outreach volume per rep at 50 contacts per week - Every segment must lead with [WHAT_CHANGED] but adapt the angle per cohort - No segment uses more than a 3-touch sequence — overworking dead leads is wasted effort - Include explicit 'drop the rest of the sequence if they reply' rules - Plan must be assignable Monday morning — concrete, not strategic mush Markdown plan with these sections: Segments | Sequences | Owners & Timeline | Metrics | Week 1 To-Do.
Variables
[AGENCY_NAME]Your agency[SERVICES]Your services[QUARTER]Which quarter[CAMPAIGN_THEME]Single theme anchoring all segments[SEGMENT_LIST_WITH_VOLUMES]List of cold segments + approx counts[WHAT_CHANGED]The anchor change that justifies reaching out[TEAM_AVAILABLE]Who can execute (reps, founder, ops)[PRIMARY_METRIC]What success looks like (booked calls, replies, revenue)[TOOLS_AVAILABLE]ESP, CRM, sequencer, etc.
Example input
AGENCY_NAME=Cinder Co, SERVICES=full-funnel paid + lifecycle for ecom, QUARTER=Q3, CAMPAIGN_THEME=we now offer a 90-day proof sprint at fixed scope, SEGMENT_LIST_WITH_VOLUMES=Closed-lost deals 6-18 months old (120), Churned clients past 12 months (28), Demo no-shows YTD (44), Newsletter MQLs no reply 60+ days (310), WHAT_CHANGED=new 90-day proof sprint, fixed $18k, with a guaranteed lift benchmark or partial refund, TEAM_AVAILABLE=2 AEs, 1 founder, 1 ops, PRIMARY_METRIC=15 booked discovery calls in 90 days, TOOLS_AVAILABLE=HubSpot + Instantly + Loom
Example output
## Segments 1. Closed-lost 6-18mo (120) — AE-owned 2. Churned clients (28) — Founder-owned 3. Demo no-shows YTD (44) — AE-owned 4. Cold newsletter MQLs (310) — Ops-owned bulk ## Sequences (all anchor on 90-day proof sprint) - Closed-lost: Email > Loom > A/B/C close - Churned: Founder email > rebook offer > drop - No-shows: Loom recap > A/B/C - MQLs: Newsletter-style note > resource > drop ## Owners & Timeline - Weeks 1-2: Segments 1+2 (high-intent first) - Weeks 3-6: Segment 3, ramp Segment 4 - Weeks 7-12: Reply triage + booked-call conversion ## Metrics - Primary: 15 booked discovery calls - Guardrails: reply rate >8%, unsub <1%, drop-if-reply enforced ## Week 1 To-Do - Mon: Ops pulls all 4 segments into HubSpot lists - Tue: AEs draft 5 sample emails per segment for founder review - Wed: Founder records 1 Loom for churned-client segment - Thu: Launch Segments 1+2 (cap 50/rep) - Fri: First reply triage + log
Pro tips
- Anchor every segment to ONE change — running 4 different value props in parallel dilutes the campaign and confuses reporting
- Have the founder personally own the churned-client segment — delegation kills win-back conversion here
- Track 'drop-if-reply enforcement' as a metric — reps who keep sending after a reply tank the whole campaign
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