Outbound Squad Biggest mistake when re-engaging closed/lost opps
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Nov 25, 2025 Clara Johnson, Head of Training at Outbound Squad, shares her sales enablement expertise to help businesses revive closed-lost opportunities. She emphasizes that these accounts are low-hanging fruit waiting for the right approach. Clara discourages routine follow-ups, urging urgency-driven outreach instead. She promotes using AI for personalized messages based on past interactions and highlights the importance of treating old prospects like fresh leads. The key takeaway? Leverage time-based insights and past context to recreate genuine interest.
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Treat Closed-Lost As New Opportunities
- Re-engage closed-lost deals as if they are new accounts by doing fresh research and finding current triggers.
- Use previous deal history only as a relevance signal, not the full playbook for outreach.
Use Time-Based Insights, Not Calendar Hope
- Swap calendar-based follow-ups for urgency-driven outreach using current company signals.
- Tie your message to specific changes (hiring, new markets) and ask about their current plans.
Avoid Feature-First Outreach
- Avoid generic product-update emails that focus on your features and ask for time.
- Instead, make outreach about the prospect's problems and new context.