Objective
Identify and act on re-engagement opportunities hiding inside your closed-lost pipeline by pulling relevant insight from call transcripts and CRM notes beyond what’s listed in the “Closed Lost” reason field.
Tools Needed
- Salesforce CRM – Access to Opportunities, Notes, and Activity History
- Gong – Access to call recordings and transcripts
- Google Sheets or Excel – To organize findings and track activity
- Email + Calendar Access – To review past communication and meetings
Step-by-Step Instructions
1. Extract Closed-Lost Opportunities
- Go to the Reports tab in Salesforce.
- Create a new Opportunities report.
- Apply these filters:
- Stage = "Closed Lost"
- Closed Date = between 6–18 months ago
- Run and export the report as a CSV.
2. Categorize Loss Reasons
- Open the CSV in Google Sheets or Excel.
- Add a column labeled “Loss Reason Category.”
- Review each "Loss Reason" field and bucket into categories like:
- Budget constraints
- Timing issues
- Project prioritization
- Stakeholder changes
- Other (add a note)
3. Review CRM Notes for Context
- In Salesforce, open each opportunity and review:
- Activity History
- Opportunity Notes
- Look for context that wasn’t included in the structured field, such as:
- Mentions of future initiatives
- Comments about timing (“Circle back in Q3”)
- Concerns or questions about pricing, feature gaps, or implementation
- Any blocker or internal champion dynamics
4. Analyze Gong Call Transcripts
- Go to Gong and open call transcripts for the opps you pulled.
- Search for phrases like:
- “Revisit”
- “Budget reset”
- “After the new year”
- “Let’s follow up”
- Log any insight about timing, objections, org changes, or interest levels.
- Pay special attention to stakeholder mentions (e.g. “My VP will want to see this”).
5. Build a Re-engagement Tracker
Create a Google Sheet with these columns:
- Account Name
- Opportunity Name
- Original Loss Reason
- Additional Context from Notes
- Quotes from Gong or Email
- Suggested Revisit Timing
- Key Stakeholders Mentioned
- Proposed Re-engagement Play
- Outreach Status (Not Started / In Progress / Replied)
6. Draft Personalized Outreach
For each opp, write a custom email using what you uncovered. Your message should:
- Reference what was said or agreed to (e.g., “You mentioned revisiting after [project]”)
- Acknowledge the past blocker, and offer a new angle
- Propose a clear next step like a quick call, update, or async response
Example:
“You mentioned budget constraints last year and suggested we reconnect in Q2 once priorities shifted. Wanted to follow up to see if anything has changed?”
7. Log Activities and Monitor
- In Salesforce:
- Log emails or calls under the Opportunity
- Create a follow-up task if no response in 5–7 business days
- Update the re-engagement tracker to reflect activity and results
Why This Matters
Without Insider AI:
- Context lives in dozens of places, invisible to most teams
- Follow-ups are manual, slow, and inconsistent
- Pipeline is left on the table
With Insider AI:
- You uncover high-context re-engagement opportunities automatically
- Reps are notified when timing and context align
- You scale what already works without scrambling every quarter
