Deal-at-Risk Detection
Save motions triggered earlier
By the time a deal is officially "at risk" — pushed a quarter, gone dark, lost to competition — it's too late to save. The signals that would have caught it two weeks earlier are all in the CRM and the engagement tools, but nobody looks at every deal every day. The manager finds out in the forecast call, when the rep says "pushed to next quarter" for the third week running.
An hour-by-hour walkthrough.
Step by step.
- 01
Score every open opportunity daily
Pull every open opportunity above the threshold. Run the health check: champion activity, multi-threading, time-in-stage, close-date slips, competitor mentions, sentiment.
Salesforce · HubSpot · Gong · Outreach - 02
Cross-check against engagement + call intelligence
Gong / Chorus transcripts give competitor mentions, sentiment, pricing pushback. Outreach / Salesloft gives cadence-response rates. LinkedIn Sales Navigator gives champion job-change signals — a champion leaving is often the earliest warning.
Gong · Chorus · Outreach · LinkedIn Sales Navigator - 03
Flag + explain + suggest action
Two thresholds crossed flips to at-risk. Rev writes an annotated note on the opportunity naming each signal, then DMs the rep with a suggested next-best-action grounded in what similar recovered deals did.
CRM notes · Slack DM · Teams - 04
Draft recovery plan on confirmation
Rep confirms → Rev drafts recovery plan: exec sponsor email (drafted, waiting for send), product involvement request (drafted, waiting for send to PM), discount analysis (numbers only, not sent). Rep edits and dispatches.
CRM · Email · Slack · Approval flow - 05
Track outcomes + feed the model
Every flag closes as: recovered, lost, dismissed-false-positive, or graceful-stall. Outcomes feed the model weekly; false positives tune thresholds; recovered patterns become suggested plays.
Data warehouse · Model retrain
What you connect to make this run.
Salesforce · HubSpot
read+writeRead opportunity + activity + contact data. Write the health-check note + at-risk flag back so pipeline reports and dashboards see the same signal.
Gong · Chorus
readCall transcripts + sentiment + competitor mentions. The single strongest signal is "customer said a competitor's name twice or more on the last two calls."
LinkedIn Sales Navigator · News APIs
readChampion job-change alerts + company news (layoffs, funding, acquisition). External signals that the CRM never sees.
Slack · Teams · Email
writeRep DM with signals + suggested action. Manager cc on high-value at-risks. Drafted recovery emails staged in the rep's outbox for review.
Before and after, honestly.
Playbooks that pair with this one.
Answers about this playbook.
Won't this cry-wolf on every deal that has a slow week?
Threshold is two independent signals, not one. A quiet week alone doesn't flag; a quiet week plus a competitor mention plus a close-date slip does. Weekly digest surfaces the false-positive rate and lets you tune.
How does it handle enterprise deals with slow, deliberate cycles?
The scoring model is stratified by ACV band. Enterprise deals get a longer baseline — 21 days of champion silence is normal for a 12-month cycle, not for a 30-day one.
Can reps opt out of certain deal types?
Yes — deals tagged as strategic / long-cycle / partner-led can be excluded from auto-DMs and only flagged in the manager's weekly review. Rep + manager set the policy per team.
What if the champion actually left the company?
LinkedIn signal fires the moment their profile updates. Rev drafts a "transition play": intro request to their replacement, farewell note to the champion, updated stakeholder map. Manager cc'd because these are high-mortality events.
Does this replace the manager's 1:1 with the rep?
No. It replaces the part of the 1:1 that's "walk me through your pipeline" — the answers are already in the dashboard. The 1:1 becomes about the plays: what did you try, what will you try next, what do you need from me.
See it run on your data.
Free plan, no credit card. Connect the systems this playbook needs and run it against a past event first.