7 Sales Outreach Strategies to Re-Engage Ice-Cold Prospects

September 8, 2015 Michael Simone

sales enablement cold prospects

In this age of SaaS sales, there is nothing more frustrating for reps than watching a once-engaged prospect fall into complete silence—to go from piping hot to ice cold.

We’ve all been there. We can see they’ve been reading our emails and clicking our links (thanks to Sidekick), viewing our website (thanks to HubSpot), but for some reason we can’t seem to get a response. 

Pick up the phone one last time and try reaching out to your ice-cold prospect, and if that doesn’t work, it might be time to try something new. But before I dive into some of the re-engagement strategies that have proven quite effective for me, I feel like it’s important to mention one thing: 

The days of ABC are over. I loved Glengarry Glen Ross, but "Always be Closing" has been replaced with "Always be Helping".

That makes good, relevant, and timely content a salesperson’s best friend, and is pivotal to some of the techniques I’ve listed below for re-engaging your coldest contacts.

Send an email that has nothing to do with your product

Isn’t it nice to sometimes get emails that take your mind off work, even if it’s for 10 seconds?

Assuming that you’ve spent some time building rapport with your prospect, send them something based on their interests outside of work. Everyone loves a break from the day-to-day grind! Here’s an example of a prospect in Chicago that I emailed prior to attending an event there:  

Be easy to talk to and assure prospects they're replying to a person, not a pitch.

Stop calling, stop emailing, start social media-ing

In 2015, email inboxes fill up faster than an I-hate-Kanye-West convention. In 2015, people rarely answer their phones. These are the harsh realities of the age we live in! 

But one thing I do know is that my Twitter DMs and LinkedIn InMail are far less cluttered. When I get a message on Twitter or LinkedIn, I can’t open it up fast enough. As a millennial and self-diagnosed smart phone addict, I need it! Try sending your prospect a message on one of those platforms instead. 

Unlike their email inbox, which might sit at 1383+ unread messages, people are more likely to still get that small rush of excitement and increase in endorphin levels from the “ding” of a social media notification.

Sales reps that use social media are actually 50% more likely to crush their quota.  

Google Alerts is a great tool for finding conversation-starters based on recent activities or achievements. These alerts can actually tell you when somebody is mentioned or active on the web, which you can use in your outreach. 

Add a little humor—it almost never fails

It’s easy to understand why this one works, but not so easy to execute! I’m going to go ahead and assume most people like laughing—so make them laugh!

I love using sites like Giphy and memes.com to find or create funny things to send prospects who were once hot.

Or take it further and send them a funny picture or video of yourself! Here’s a good example from my colleague, Anna:

sales outreach humor

Change up your timing

This one can be really effective, so try it: Email your prospect on the weekend, and see if that gets you a response!

People get way less emails on the weekend, so hit them when they don’t expect it. You can always use tools like Sidekick or Streak to write the email during work hours, and schedule it to deliver a day or two later.

You’d be amazed at the kind of results you’ll get! This is especially effective for Executive level prospects.

Here's a tip: Make sure your email is short enough to read on an iPhone 5 screen. From what I've seen, most people check emails on their phone over the weekend!

Think outside the box and use your other talents

Anybody can write a boring “Just checking in” email (PS – don’t ever use that line). But putting your own creativity and flare into your follow-ups will really grab people's attention.

You're not only a sales rep. What other talents are you hiding? Do you play the guitar or know how to edit video? Incorporate it into your selling style. 

One of my colleagues, Matt, is pretty good with Photoshop, so he’ll Photoshop himself into the prospect’s LinkedIn photo.

Sometimes I'll even write up a “Top 5 Reasons Why You’ve Gone Silent”, suggesting tongue-in-cheek that perhaps the prospect has been partying too much lately to respond.

Make your outreach so hyper-personalized, they can't ignore it

I hope this one is obvious, but you should make your prospect feel like they’re the single most important potential customer.

Insanely deep personalization in your messaging can really seal the deal:

  • Recommend pieces of content based on what they’re tweeting about. 
  • Recommend they join LinkedIn groups based on their interests.
  • Use Datanyze and other tools to get insight into what tech your prospect is using.

Convince them that you’ve gone above and beyond your daily job to make them feel valued. 

“Should I Stay or Should I Go?"—Know when they're not interested

The truth is that not every prospect is going to become a customer, and this last tactic is about helping you identify when there's potential and when it's a lost cause.

As a salesperson, you should be looking to qualify or disqualify opportunities as quickly as possible.  It is not worth the time—for you or your contact—to pour hours of work into a prospect that will never be interested in using your product or service. 

So how can you get that answer from them? Be upfront about it. These emails get incredible response rates. Even if the answer is “no, I’m not interested”, that’s fine! It’s better you know that so you can move on.

But before you get to that point, try to humanize your outreach and differentiate yourself as a sales rep by getting personal with the tactics I mentioned above. You'll have better luck warming up to your coldest contacts.  

Learn how to get your Sales team to close more with content in our free eBook!

About the Author

Michael Simone

Michael is a Senior Account Executive at Uberflip helping modern marketers crush their content ROI targets by day. By night, you can find him cheering on Toronto's sports teams, or trying a new restaurant and plotting his next world adventure with friends.

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