# Win-Back Email Sequence: Inactive Trial Users

**Status:** Ready for implementation  
**Created:** 2026-04-14  
**Owner:** Lifecycle Marketing (Dex)  
**Launch deadline:** Today — before pricing update goes live 2026-04-15  

---

## Sequence Overview

| Attribute | Detail |
|---|---|
| Audience | `inactive_trial_user` — trial started, no milestone activity for 4+ days |
| Entry trigger | User has been inactive for 4 consecutive days during 14-day trial |
| Exit conditions | User completes all 3 activation milestones **OR** converts to paid **OR** completes email 4 |
| Suppression | Exclude `converted_user`; suppress if user reactivates between sends |
| Cadence | 4 emails over 9 days (Day 0 → Day 2 → Day 5 → Day 9 from inactivity trigger) |
| Channel | Email only |

### Why This Sequence

- Inactive-by-day-4 rate has climbed from 31.3% → 51.6% over the last 12 cohort weeks.
- Trial-to-paid conversion dropped from 15.4% → 7.9% over the same period.
- Most users complete CRM connection (event 1) but stall before publishing a playbook (event 2) or inviting a teammate (event 3).
- The existing day-3 "tips" email is generic (6% CTR, no measurable activation lift) and doesn't branch on inactivity.
- There is no dedicated re-engagement flow for users who go quiet.

### Activation Milestones (Reference)

1. Connect CRM data source ✅ *(most inactive users have done this)*
2. Publish first automation playbook ❌ *(primary stall point)*
3. Invite at least 1 teammate ❌

---

## Email 1 of 4 — Inactivity Check-In

**Send:** Day 0 (inactivity trigger fires — 4 days with no milestone activity)  
**Goal:** Restart attention; acknowledge friction; point to the single next step  
**CTA objective:** Get user back into the product to publish their first playbook  

| Field | Content |
|---|---|
| **From** | Dex at QueuePilot |
| **Subject** | Still setting up QueuePilot? |
| **Preview text** | Your CRM is connected — publishing your first playbook takes about 10 minutes. |

### Body

> Hey {{first_name}},
>
> You connected your CRM to QueuePilot a few days ago — that's the hardest part done.
>
> Most teams stall at the same spot you're at: figuring out what to automate first. You don't need to start from scratch.
>
> We have prebuilt playbook templates for the most common RevOps and CS workflows — onboarding handoffs, renewal alerts, pipeline stage changes. Pick one, customize it, and publish in about 10 minutes.
>
> **[Publish my first playbook →]**
> *(link: app deep-link to playbook template gallery)*
>
> If something's blocking you, reply to this email. I read every response.
>
> — Dex

| Metric | Target |
|---|---|
| Open rate | ≥ 45% |
| CTR | ≥ 12% |
| Reactivation within 72h | ≥ 8% of recipients |

---

## Email 2 of 4 — Quick-Win Template Shortcut

**Send:** Day 2 after trigger (if still inactive)  
**Goal:** Lower perceived effort with a specific, copy-paste template  
**CTA objective:** Get user to launch a prebuilt playbook in one click  

| Field | Content |
|---|---|
| **From** | Dex at QueuePilot |
| **Subject** | Your first workflow is one step away |
| **Preview text** | The CS Handoff playbook is ready to go — just hit publish. |

### Body

> {{first_name}}, here's the fastest path to a working automation:
>
> **The CS Handoff Playbook** — our most-used template for teams your size.
>
> What it does:
> - Detects a new CRM deal moving to "Closed Won"
> - Creates an onboarding task for the CS owner
> - Sends the customer a personalized welcome sequence
>
> Setup time: under 10 minutes. No code. No custom fields needed.
>
> **[Use the CS Handoff template →]**
> *(link: app deep-link to CS Handoff playbook template)*
>
> Once you publish, you'll see live activity in your dashboard within the hour.
>
> — Dex

| Metric | Target |
|---|---|
| Open rate | ≥ 38% |
| CTR | ≥ 10% |
| Reactivation within 72h | ≥ 6% of recipients |

---

## Email 3 of 4 — Proof + Objection Handling

**Send:** Day 5 after trigger (if still inactive)  
**Goal:** Reduce perceived risk/effort with peer social proof  
**CTA objective:** Get user to see a concrete peer result and take action  

| Field | Content |
|---|---|
| **From** | Dex at QueuePilot |
| **Subject** | How a 90-person SaaS team launched in 1 day |
| **Preview text** | They automated their entire onboarding handoff — starting from the same step you're on. |

### Body

> {{first_name}}, I get it — evaluating new tools when your team is already stretched is hard.
>
> Here's what happened when the RevOps team at a 90-person SaaS company picked up QueuePilot at the same stage you're at now:
>
> - **Day 1:** Published the CS Handoff playbook (the same template sitting in your account).
> - **Day 2:** Invited their CS lead and ran a live handoff.
> - **Week 1:** Eliminated 6 hours/week of manual CRM-to-Slack copy-paste across the team.
>
> They started with one playbook, not ten. You can do the same.
>
> **[Copy their setup — publish in 10 min →]**
> *(link: app deep-link to playbook template gallery)*
>
> Want a hand? Reply here or grab 15 minutes with our onboarding team: [Book a quick setup call →]
>
> — Dex

| Metric | Target |
|---|---|
| Open rate | ≥ 35% |
| CTR | ≥ 8% |
| Reactivation within 72h | ≥ 5% of recipients |

---

## Email 4 of 4 — Last Call + Opt-Out

**Send:** Day 9 after trigger (if still inactive — typically day 13 of trial, 1 day before expiry)  
**Goal:** Capture final conversion intent or cleanly suppress  
**CTA objective:** Activate now or stop reminders  

| Field | Content |
|---|---|
| **From** | Dex at QueuePilot |
| **Subject** | Trial ends tomorrow — keep your progress? |
| **Preview text** | Your CRM connection and templates are still here. One step to keep them. |

### Body

> {{first_name}}, your QueuePilot trial expires tomorrow.
>
> Here's what's saved in your account right now:
> - ✅ CRM connection (live)
> - 🔲 First playbook (ready to publish)
> - 🔲 Teammate invite (one link away)
>
> If you finish setup today, your automations start running immediately — and you keep everything when you move to a paid plan.
>
> **[Finish setup and activate →]**
> *(link: app deep-link to activation checklist)*
>
> Not the right time? No problem — click below and we'll stop the reminders.
>
> [Pause trial reminders →]
>
> — Dex

| Metric | Target |
|---|---|
| Open rate | ≥ 42% |
| CTR (primary CTA) | ≥ 9% |
| CTR (opt-out link) | tracked separately |
| Direct conversion from email | ≥ 2.5% |

---

## Sequence-Level Targets

| Metric | Target | Current baseline (no win-back) |
|---|---|---|
| Full-sequence reactivation rate | ≥ 15% of entered users | 0% (no sequence exists) |
| Trial-to-paid lift for recipients | +3-5 pp vs. control | 8.1% current overall |
| Unsubscribe rate per email | < 0.5% | — |
| Suppression via email 4 opt-out | Tracked, not a failure metric | — |

---

## Segmentation + Suppression Logic

```
ENTER sequence IF:
  event = trial_started
  AND days_since_last_milestone_activity >= 4
  AND segment != converted_user
  AND NOT currently_in_sequence("winback-inactive-trial")

ADVANCE to next email IF:
  still inactive at scheduled send time

EXIT sequence IF:
  user completes ALL 3 activation milestones
  OR user converts to paid
  OR user clicks "Pause trial reminders" (email 4)
  OR email 4 is sent (sequence complete)

SUPPRESS:
  converted_user at all times
  Users who reactivate between sends (re-evaluate at each send)
```

---

## Implementation Notes

1. **Pricing context:** The pricing update ($79 → $99/user/month on Starter) goes live 2026-04-15. This sequence does **not** reference specific pricing — intentionally. Users in the win-back flow should convert on activation value, not price anchoring. If a pricing-specific campaign is needed, it should be a separate one-off send layered on top, not mixed into this behavioral sequence.

2. **Day-3 generic tips email:** Once this sequence is live, suppress the existing day-3 "tips" email for any user who enters the win-back flow. The two should not overlap. Long-term, consider retiring the day-3 email entirely and replacing it with milestone-aware sends for all trial users.

3. **Deep links:** Every CTA should deep-link to the specific in-app screen (playbook template gallery, activation checklist) — not the generic dashboard. Work with engineering to confirm deep-link URLs before launch.

4. **Reply handling:** Emails 1-3 invite replies. Route replies to Dex or the lifecycle team inbox so they can be triaged within 4 business hours.

5. **Weekend signups:** Weekend signup rate has risen to 31% and those users activate more slowly in the first 72 hours. Consider a future iteration that delays the inactivity trigger by +1 day for Saturday/Sunday signups to avoid firing the sequence prematurely. Not blocking for today's launch.

6. **A/B testing (post-launch):** After 2 full cohort weeks (~500 sequence entries), test:
   - Email 1 subject line: "Still setting up QueuePilot?" vs. "Your playbook is waiting"
   - Email 2 template choice: CS Handoff vs. Renewal Alert playbook
   - Email 4 urgency framing: "Trial ends tomorrow" vs. "Keep your CRM connection"

---

## Sequence Visual

```
[trial_started]
     │
     ▼
[Existing welcome email - immediate]
     │
     ▼
  4 days no milestone activity?
     │            │
    NO           YES
     │            │
     ▼            ▼
  (continue   ┌─────────────────────────────────┐
   normal     │  WIN-BACK SEQUENCE               │
   trial      │                                   │
   flow)      │  Email 1 (Day 0) Check-In         │
              │       ↓  still inactive?           │
              │  Email 2 (Day 2) Quick-Win         │
              │       ↓  still inactive?           │
              │  Email 3 (Day 5) Social Proof      │
              │       ↓  still inactive?           │
              │  Email 4 (Day 9) Last Call/OptOut  │
              └─────────────────────────────────┘
                        │
              EXIT if: activated / converted / opted out
```