With an average win rate of 47%, more than half of sales opportunities are marked as closed-lost. But a lost deal doesn’t have to stay lost. Many prospects simply aren’t ready to buy yet. But by using the right tools, reaching out at the right time and applying proven tactics, businesses can successfully re-engage these prospects and turn missed opportunities into new wins.
In this blog, we’ll cover the strategies that work for winning back closed-lost deals: tools, timing, and tactics.
Revisiting these deals can be one of the most efficient ways to generate revenue. Unlike cold leads, closed-lost prospects already know who you are and what you offer. You've had conversations, built some level of trust and possibly even uncovered some of their pain points. This makes re-engagement faster and more cost-effective than starting from scratch.
More importantly, circumstances change. The competitor they chose might not have lived up to expectations. A new decision-maker could be in place. Budgets might have been approved, or a business challenge could have become more urgent. When you circle back with the right message at the right time, you put yourself in a strong position to be reconsidered.
Looking at closed-lost deals not as failures, but as delayed opportunities, allows your team to work smarter - reviving pipeline without relying solely on brand-new leads.
Re-engaging lost deals is a strategic process that, when timed correctly, can breathe new life into your sales pipeline. The best time to re-engage a lost deal depends on several factors, including the reason for the loss, the sales cycle length, and external business or market conditions. Here's a breakdown to guide your timing and approach:
Best for: Deals lost due to missing features or capabilities. If you've enhanced your offering or addressed past objections, this is a prime time to reach out. Highlight the improvements and how they directly resolve their previous concerns.
Example:
"We’ve recently rolled out new features that align with what you were looking for earlier this year—would love to show you what’s changed."
Best for: B2B deals with structured procurement cycles. Many businesses re-evaluate vendors and tools quarterly or bi-annually. Reaching out just before budgeting or strategic planning windows increases the chance of being reconsidered.
Example:
"As you're planning for Q3, are you revisiting any tech or process improvements? Let’s revisit our conversation from earlier this year."
Best for: Deals lost due to timing, budget, or external priorities. If industry dynamics change—like increased demand, new regulations, or budget resets—it could create a renewed need for your solution.
Example:
"With the recent shift in [industry trend], we’re seeing companies like yours revisiting tools that streamline [X]. Is this something you’re exploring again?"
Best for: Deal loss due to internal changes or misalignment. Monitor the prospect’s business activity (new funding, leadership changes, hiring trends, etc.). These are key indicators they may now be in a better position to reconsider.
Example:
"Congrats on the new VP of Sales! We spoke earlier this year—might now be a good time to reintroduce how we can support your growth?"
Best for: Deals lost to a competitor. By this point, the competitor’s solution will have either proven itself or under-delivered. It’s a tactful moment to check in.
Example:
"Just checking in—how is [Competitor] working out for you? If it’s not meeting expectations, we’d be happy to revisit your goals together."
Winning back closed-lost deals requires more than just timing and good intentions, it demands consistency, coordination, and the ability to scale your efforts across dozens (or hundreds) of leads. That’s where the right tools come in. They help you track, automate, personalise, and optimise every stage of your re-engagement strategy - without letting anything fall through the cracks!
HubSpot is a standout tool for this. With its powerful CRM at the core, you can easily track closed-lost deals, segment them based on the reason they were lost and set up automated workflows to re-engage them over time. Let's review some of our favourite features to use for re-engagement:
1. HubSpot CRM – Deal Management & Smart Views
Tag and segment lost deals by loss reason or close date. Create filtered views (e.g., “Deals Lost in Last 90 Days”) and set task reminders for follow-ups.
2. Workflows (Marketing & Sales Hub Pro/Enterprise)
Automate follow-up emails or task assignments based on deal properties like “Closed-Lost” or specific loss reasons. Example: Send a tailored email 90 days after a deal is lost.
3. Sequences (Sales Hub Pro/Enterprise)
Enroll contacts into automated email sequences with reminders for manual follow-up. Example: A 3-step win-back email series with updates, value reminders, and a call CTA.
4. Lead Scoring
Assign points to actions like revisiting the website or engaging with emails. Alert reps when a previously lost lead becomes active again.
5. Marketing Email with Smart Content
Use smart rules to change email content based on lifecycle stage, list, or behaviour. Example: Show product updates to contacts lost due to missing features.
6. Playbooks (Sales Hub Pro/Enterprise)
Create templates for sales reps to follow during re-engagement calls. Customise by loss reason or persona to maintain consistency and quality.
7. Custom Properties & Reporting
Track data like “Re-engagement Attempt Date” or “Recovery Status.” Use dashboards to identify which types of deals are most recoverable and why.
8. Breeze AI
Use Breeze AI and Copilot to generate personalised re-engagement emails and call scripts based on previous objections and deal history.
9. Sales Analytics Tools
Analyse trends in closed-lost deals, such as most common reasons, re-engagement timing effectiveness, and which reps are best at recovering lost deals.
Re-engaging a closed-lost deal isn’t just simply following up, it’s the need to deliver value in a new context. To revive interest and rebuild momentum, your approach needs to be strategic, relevant and timely. Here are the tactics that consistently move the needle:
Gone are the days when generic “just checking in” emails worked. In fact, research shows that emails with personalised subject lines are 26% more likely to be opened. Tailor your outreach based on the specific reason the deal was lost. Was it budget? Timing? A missing feature? Acknowledge it directly and offer a fresh angle.
People are more likely to reconsider when something has changed. This could be a new product feature, updated pricing, or a compelling case study that shows success with a similar customer. You’re giving them a reason to re-evaluate.
Ideas include:
Exclusive webinar invites
Limited-time discounts or pilot offers
Success stories from their industry
Instead of jumping straight into the sales pitch, ask meaningful questions like:
“What’s changed since we last spoke?”
“Are there new priorities we should be aware of?”
“Would it be helpful to revisit this with your new leadership team?”
These open the door to a real conversation, not a recycled sales process.
A single email won’t cut it. Winning back deals requires a mix of email, phone calls, LinkedIn messages and even direct mail. According to Koncert, it takes roughly 5-10 touches to re-engage a prospect. Diversify your outreach to stay visible and increase your odds of getting a response.
Example Flow:
Email with new offer or insight
LinkedIn message referencing that email
Follow-up call or voicemail
Direct mail piece (if applicable)
Final check-in with added value or incentive
Winning back closed-lost deals takes more than just following up - it takes insight, timing and the right systems in place. As you’ve seen throughout this blog, understanding why you lost, when to act and using tools like HubSpot can turn “no” into future revenue.
Want to see more on how to use HubSpot to win closed-lost deals? Watch our webinar, Winning Closed-Lost Deals Again, and learn how to capture insights, spot patterns and turn lost deals into wins with powerful tools.