The 25-Day Plan to Revive Closed-Lost Opportunities
Step-by-step outreach tactics for getting back in the door
DEAR STAGE 2: Our product has come a long way over the last 18 months and I think there’s more we can be doing to nurture the opportunities in the past. What’s the best way to reengage lost opportunities? ~SECOND CHANCES
DEAR SECOND CHANCES: We’ve all been there—watching a promising deal slip away and land in the “closed-lost” column. But here’s the thing: a lost deal today isn’t necessarily a lost deal forever.
Dave Bentham, VP GTM at DinMo, knows a thing or two about turning old opportunities into new wins. His approach? A structured, multi-touch process that doesn’t rely on luck—it’s about timing, persistence, and delivering the right message at the right moment.
Here’s a step-by-step playbook you can try today:
Step 1: Find Your Closed-Lost Deals and Understand Why They Died
Start with the closed-lost reason. Pull up past opportunities and categorize them. Was budget the issue? Did they go with a competitor? Was it a product fit concern? You might this tagged in your CRM already, but if you’re it can also help to go back and listen to call recordings to understand what challenges they were trying to solve at the time.
💡 Outreach tip: Your first message should be personalized based on what you uncover. If they didn’t have budget before, but you see they’ve recently raised funding, that’s your angle. If they chose a competitor, highlight new features that might change the equation.
Step 2: Identify Triggers That Make the Timing Right
What’s changed on the buyer’s end since you last connected? Start by looking for changes in the buying committee. Did someone new move into a decision-making role? A fresh perspective could be your way back in. Any other changes at the company level? Have they raised a funding round? If budget was the blocker, they might now be ready to talk. What other activity is taking place? Maybe they are engaging with content related to your solution, have liked a LinkedIn post or restate company goals. These are small signals that could mean they’re back in the market.
Step 3: Activate a Multi-Touch Cadence
Now that you’ve done your research, it’s time to execute. A structured outreach cadence ensures you stay persistent without being annoying. Here’s what Dave recommends:
Day 1: Triple Touch (LinkedIn, Phone, Email) - Hit all three channels at once to maximize your chance of a response.
Day 4: Call First, Email Second -The phone is your best tool to gauge interest quickly. Reference the reason they passed last time and why things might be different now.
Day 6: Educate With Email & Phone - They might not remember your product. Share updates on new features that address their previous concerns.
Day 8: Expand Your Reach - If your original contact isn’t responding, call other members of the buying committee. Deals rarely happen in a vacuum.
Day 10: LinkedIn Engagement - Build 1:1 relationships by commenting on their posts, sending voice notes, or using InMail.
Day 15: Video Email + Phone - Send a short video demo of new features. A personalized video increases engagement.
Day 17: Follow Up on the Video - Call to see if they had time to watch. Keep the conversation going.
Day 30: The Open-Ended Goodbye - If there’s still no response, send a short and polite email keeping the door open for future conversations.
Too often teams treat closed-lost deals as dead forever.
The reality?
Most lost opportunities will be back in the market sooner than you think. If you stay proactive and top of mind,, you’ll be the first one they call when they’re ready to buy.
Until next week!