Playbooks

Playbook Reviewed · not yet fact-checked

Situation

Your CRM holds deals marked closed-lost 6–18 months ago. They evaluated you seriously, then walked away over timing, budget, or a competitor — and nobody has touched them since. Circumstances change: budgets reset, champions move, the chosen vendor underdelivers. This pipeline already knows who you are, which makes it the warmest untouched list you own.

Who this is for

The play

1. Targeting

Pull closed-lost deals from the last 6–18 months. Exclude anything lost on fit — "wrong product", "no need" — because nothing has changed for those. Split the rest into three segments by loss reason: timing, budget, competitor. Import each segment as its own list so messaging stays segment-specific, and let deduplication reconcile contacts already in your workspace.

A list this old has decayed, so validate it before anything sends. Reply's email validation marks each address Valid, Risky, or Invalid: treat Risky as valid but keep Risky addresses to no more than 20% of what you send to avoid high bounce rates, and Reply does not send sequence emails to Invalid addresses at all. See prospect data.

2. Sequence structure

When you add steps, Reply pre-fills the delay between them — 0 days before the first step, then 2, 4, and 7 days for the next insertion positions. Weekends count, and one day of delay is 24 hours. Lengthen the delays in the step editor if you want a slower pace.

3. Messaging angles

• Timing losses — "you said the timing was wrong; here is what changed on our side since"
• Budget losses — lead with a lower-commitment starting point or new ROI evidence, not a discount
• Competitor losses — ask how the chosen tool worked out; a meaningful question focused on their situation is useful either way
• Every message references the original evaluation — this is a warm thread, not cold outreach
• Give every follow-up a concrete reason to exist and something of value to add; a follow-up with no reason reads as pressure
• Send the breakup only after a couple of follow-ups, when you really mean it — Reply's documented example subject line for this message is "Permission to Close Your Account?"

4. Timing and cadence

On the default delays the four steps fit inside roughly two weeks; stretch them if that feels rushed for your deal size. Run one segment at a time so you can compare messaging, and keep sends inside your normal windows and limits — see sending schedules. After the sequence ends, filter the non-repliers by number of email views: prospects who kept opening but never answered are the documented retargeting cohort — move them to a re-nurturing sequence with fresh content, call them, or connect on social instead of re-running the same message.

5. Handling replies

Route interested replies to the deal's owning AE the same day they arrive — the prior relationship is the asset, so the familiar name should answer. Reply's reply classification separates interested from not-now; park not-now replies in a follow-up list with a date instead of letting them vanish again. The sequence stops automatically on any reply — see sequence stopping. If you run this motion through Jason AI, Re-engagement follow-ups configured in the knowledge base can revive threads that go quiet — each one fires a set number of days after the last reply, in Auto or Draft mode. See the AI SDR model.

Templates

The templates below are illustrative examples, not sourced product templates. Double-brace placeholders are Reply variables; nonstandard ones like {{LostQuarter}} must exist as custom fields before launch.

Subject: {{Company}} + {{MyCompany}} — worth another look?

Hi {{FirstName}},

When we spoke in {{LostQuarter}}, the timing wasn't right on your side.
Two things have changed since then that I think matter for {{Company}}:

1. {{ChangeOne}}
2. {{ChangeTwo}}

Worth a fresh 20 minutes, or should I close the file?

{{SenderName}}

Subject: how did {{CompetitorName}} work out?

Hi {{FirstName}},

You went with {{CompetitorName}} back in {{LostQuarter}} — a fair call at
the time, and I'm not writing to relitigate it.

Genuine question: did it solve {{OriginalProblem}}? If yes, I'll close the
file. If parts still hurt, that's exactly what we've rebuilt since — happy
to show you what changed.

{{SenderName}}

Expected results

Common mistakes

• Sending one generic "checking in" message to all loss reasons at once
• Skipping validation on a list that has aged 6–18 months, or sending a segment that is more than 20% Risky addresses
• Including deals lost on product fit — nothing changed for them
• Writing as if the relationship never existed, forcing the prospect to re-explain context
• Letting interested replies sit unassigned instead of routing them to the owning AE
• Re-running the play on the same contacts every quarter until they unsubscribe

Build this in Reply

1. Export closed-lost deals with loss reason and owner from your CRM, or pull them through a CRM sync.
2. Import contacts into one list per loss reason — contact management covers fields and ownership.
3. Validate the addresses: on the People page, select the contacts and click Validate emails (one batch at a time). Keep Risky under 20% of the send; Invalid addresses are excluded from email steps automatically.
4. Create a sequence per segment using the four steps above — Reply pre-fills the delays; structure guidance in sequence design.
5. Launch one segment first and confirm enrollment picked up the list.
6. Process replies daily and hand interested threads to the owning AE — reply management covers the routing. Afterward, filter non-repliers by email views and move the engaged ones to a re-nurture sequence.

Related

• Re-engage a cold contact database — the same muscle applied to contacts rather than deals
• Sequence design
• Process positive replies
• Reply classification
• Bounce handling

Build with Reply

• REST API: docs.reply.io — import lists and create sequences programmatically
• MCP: agents.reply.io/mcp — agents segment contacts and launch sequences conversationally
• CLI: agents.reply.io/cli — scripted list import and launch
• Agent skills: agents.reply.io/skills — packaged outreach workflows