Best Ways to Re-Engage Old Sales Leads Through Email

While a qualified prospect didn’t close on your business at the time, this doesn’t mean they never will.
Reading Time: 7 minutes

Most companies that use B2B lead generation strategies focus almost exclusively on generating new interest. But if you’re only looking for new prospects and new opportunities, you could end up missing out on some lucrative options from the past.

If you’re willing to reach out to and re-engage with older sales leads you thought were lost, you might be able to recapture them and land new sales. Doing so would help you capitalize on relationships and leads that already exist—while simultaneously boosting your sales performance.

Here are some of the best ways to re-engage with old sales leads via email:

  • First Thing’s First—Prep Your Approach
  • Send Lead Magnets to Catch a Feel
  • Ask for Feedback Through Surveys and Polls
  • Test Different Subject Line Copy
  • Be Strategic With Your Verbiage and Timing
  • Aim to Catch Up and See What’s New
  • Let Them Know of New Additions to Your Company
  • If All Goes Well, Implement Them Into a Drip Campaign


First Thing’s First—Prep Your Approach

Everything starts with preparation. Before you start drafting an email, it’s important to do some preliminary research.

The first way to do this is to familiarize yourself with old account info. Hopefully, you have a CRM platform (or a similar tool) to keep all information on your prospects, leads, and customers organized and available to the team. If you don’t, you’ll need to rely on old conversation threads or worse, your own memory.

In any case, it’s important to familiarize yourself with this old account information. Who is this person? How did you find them or how did they find you? What made them interested in your products and services? What ended the sales conversation originally? The more information you gather, the more context you’ll have to draft your forthcoming messages.

It’s also a good idea to check social media (especially LinkedIn) to see if there are any new developments with this individual that you should be aware of. For example, did they recently get a promotion? Have they changed jobs? This can provide you with useful information while also giving you an easy way to lead into a new conversation.

Last but not least, take a moment to analyze and understand past mistakes or gaps in motivation that prevented this sales conversation from moving forward. Was there a budget issue? Did your product not have the right features? In other words, what went wrong?

At this point, you can make a determination about whether following up is worth it – since it’s not going to be worth it for every old lead. If this person was adamant about not needing or wanting your product, and nothing about their situation has changed, you would only be wasting your time by reaching out.


Send Lead Magnets to Catch a Feel

When initially reaching out, consider sending lead magnets like free pieces of content as a way to probe interest and monitor for signs of buying intent. If they download your content, or if they engage with your other lead magnets, it’s a positive sign that you can continue moving forward.


Ask for Feedback Through Surveys and Polls

Another valid approach is asking for feedback directly via polls and surveys. This is especially effective if you’re not sure why an individual decided not to move forward with purchasing your products and services.

If this person provides negative feedback, you can learn from it and act on it. If they raise concerns or complaints about your product, you may be able to use that feedback to develop the product in new ways. If their objections are no longer valid, you’ll have an excellent understanding of how to reach out to them an re-engage in this new series of interactions.

If this person provides mostly positive feedback, you’ll have a clear path to re-engagement. You may be able to pick up right where you left off.


Test Different Subject Line Copy

It’s hard to tell exactly what types of subject lines are going to work best for your old leads. That’s why it’s a good idea to test out many different types of subject lines, so you can gather data and analyze which types of subject lines work best.

No matter what, these are some subject line drafting fundamentals that can lead you to success.

  • Personalize your subject line. Keep the subject line as personal and specific as possible; make it clear that you’re specifically trying to reach this individual.
  • Keep it concise. Bloated subject lines will lead to your emails being deleted on sight.
  • Stimulate natural curiosity. A subject line like “Congratulations! I just heard…” will naturally make your lead interested in opening the message. Even if they had a recent major accomplishment, they’ll be curious to know why you’re emailing them.


Be Strategic With Your Verbiage and Timing

Be careful with your timing and verbiage to make the most positive impact on your old leads.

Timing can be tricky, since everyone has a unique schedule. Research suggests that generally, Mondays are too busy for people to respond to every email. On Fridays, people are looking forward to the weekend. You’re best off sending an email in the middle of the week. Morning and early afternoon emails perform better, but make sure you keep your old lead’s time zone in mind.

When it comes to verbiage of your emails, consider the following:

  • Focus on the relationship. Don’t immediately jump into selling a product – or you might turn this person off. Instead, focus on the relationship. Praise them for a recent accomplishment. Compliment them on a piece of content they wrote. Ask about their hobbies or family. Small talk may not be especially deep or interesting, but it gets the ball rolling.
  • Remain concise. In your first few messages, be as concise as possible. With a subject line of only a few words and a message of only a few sentences, you’ll be much more likely to get a response – and you’ll force yourself to be more mindful of the words you choose to use.
  • Start small. Any initial engagement is a positive sign. Don’t try to rush things too quickly.


Aim to Catch Up and See What’s New

One of the best ways to reach out to a previously dropped lead is to simply catch up and see what’s new for both parties. As we stressed in the previous section, it’s usually better to focus on the relationship rather than selling a product; to this end, focus on figuring out what’s new for this person. Have they advanced in the company? Have they taken on a new job title? Are they exploring new markets or new strategies?

It’s also a good idea to talk about what’s new in your position – as we’ll see in the next section.


Let Them Know of New Additions to Your Company

Companies love to pride themselves on business growth, and this reigns true for both the company reaching out and the company being prospected. If you want to re-engage old leads in the pipeline, it’s essential that you emphasize any additions or changes to your company that might be relevant to this lead. These new additions could include:

  • Product enhancements. This person may have objected to buying your product because it didn’t have enough features, or it didn’t have the features they wanted. If you’ve recently upgraded the product, or if you offer a different product that can meet their needs, this is your chance to make a pitch for it.
  • New services. The same is true if you have new services to offer. You may not have been able to meet their needs previously – but can you now?
  • Price drops/discounts. If the primary reason for this lead’s objection was price or budget, consider reaching out with information about price drops or discounts that could potentially make things work.
  • Leadership/vision changes. You may also be in a position to highlight any leadership or vision changes within your company that make it better suited to this person’s needs.


Highlighting any of these changes gives you a meaningful motivation for reaching out – and can start the conversation on a positive note. If you’ve made compelling changes to your company or products in the recent past, and you already had a good relationship with this lead, closing the sale might be a cinch.


If All Goes Well, Implement Them Into a Drip Campaign

If your initial conversations go well, you can implement this lead into an ongoing drip email campaign. From there, you can continue nurturing them, providing them with more information and resources while keeping your brand top of mind. At this point, you can treat them like other leads in the same stage of the sales funnel.


Key Takeaways

Some of your old leads are bound to be truly lost – but there are so many promising opportunities lurking in your old lead pool that it would be foolish to dismiss them as impossible to win.

With careful proactive research, a tactful approach, a focus on relationship building, and attention to new differentiators, you can win over even your oldest “lost” leads and empower your primary lead generation strategy.

Sapper Consulting is a B2B lead generation and sales consulting agency with all the tools, technologies, and experts you need to effectively manage your sales pipeline – and create a steady stream of leads.

Whether you’re more interested in re-engaging your old sales leads or capturing totally new ones, we have the expertise and resources to help you achieve your goals. Contact us to get started today!

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About Sapper Consulting

Sapper's sales prospecting team becomes a natural extension of your existing sales efforts, helping you find new leads that are a great fit for your business.

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