Re-engagement Campaign Ideas To Revive Dead Opps

Andrea Wunderlich

With the new year upon us, salespeople and marketers alike are looking to closed-lost opportunities to drum up new business. 

After all, accounts with previous opportunities have a higher chance of closing. 


  • They’re qualified — if an opp made its way into your reps’ pipeline before you already know the account is qualified.
  • They know you — your reps have an existing relationship with contacts at that account. 

Pssst.Chili Piper helps automate re-engagement campaigns. Wanna see it in action?


So, what’s a re-engagement campaign? 

A re-engagement campaign is a joint effort between marketing and sales to create new opportunities in accounts with previous closed-lost opportunities. 

Source: Tenor

Things to keep in mind 

Re-engagement campaigns can be wildly successful, but they can also be tone-deaf flops. Here are some things to keep in mind when planning your campaign: 

  • Make sure you’re in lockstep with sales.There’s nothing worse than when the right hand doesn’t know what the left is doing. Make sure you consult your sales team before executing a re-engagement campaign. 
  • Identify a segment. Don’t just blast an email out to the primary contacts at every account with a closed-lost opportunity. Your prospects can smell a spray and pray campaign from a mile away. Instead, segment your closed-lost campaign. Some segmentation ideas: closed-lost reason, industry, company size, etc. 
  • Make sure there’s a compelling event to justify your outreach. If nothing has changed at your company or in the account since your last interaction, it might not be the right time to run a re-engagement campaign.
  • Offer something valuable.The problem with most marketing campaigns is they confuse the offer with the call to action. “Get a demo” is a call to action, not an offer. A good litmus test for this is asking yourself the following question: does my prospect have to do something here? If the answer is yes, then it’s a call to action, not an offer.

  • Ray Bennett Jr., Senior Retention Marketing Manager at

"What I've seen work is to not treat re-engagement campaigns as re-engagement campaigns. Treat it as something of value to your target audience. Yes, it's B2B, but you're still selling to a person at the end of the day, so you need to ask yourself: What are their needs and what would they be using your platform for?"

  • Be mindful of the call to action. The biggest mistake you can make when executing a re-engagement campaign is asking too much of your prospect before demonstrating value. That said, “get a demo” may not be the right CTA for a re-engagement campaign. More often than not, the prospect you’re attempting to re-engage has already seen a demo of your product. What has changed between now and their first interaction with you that would make a conversation with you valuable? 

Louie Bernstein, founder of Sales Getters, adds, “Be upfront. With a call or email, let [your prospect] know you understand that, for whatever reason, the last time they reviewed your product or service, it just wasn't the right time for them.”

“That gives them an out and puts the past behind you and them. I would pause here and wait to hear their response. It will help you understand what direction to take."

Re-engagement campaign ideas 

There are endless possibilities for re-engagement campaigns. The following are some tried and true ideas sourced from our network. 

Recent funding announcement 

A recent funding round is a great opportunity to re-engage with accounts that have gone dark. But cash in hand isn’t a good enough reason to buy software. 

Funding rounds mean growth and with growth comes new growing pains. Make sure you’re connecting your solution to a new problem they’re experiencing or an opportunity they have as a result of new funds. 

“You raised some money, now come spend it with us!” is not a compelling call to action. 

These are also pretty easy to piece together with third-party data providers like Crunchbase

The compelling event:Recent funding round 

The offer: A gift to congratulate them on their recent funding 

The CTA: A short conversation with your sales team about how your product can help them solve a new challenge or capitalize on a new opportunity 

New product launch 

Have a new product that may be of interest to someone you’ve spoken with in the past? Product launches offer a solid reason to re-engage with cold prospects. 

Just make sure you’re not blasting these communications to all your cold prospects. An announcement is one thing, but a targeted campaign for dead opportunities is another. 

One way to avoid this is to pull a list of dead opportunities based on closed-lost reasons. More often than not, the new product satisfies a common request or missing functionality that’s documented in your sales team’s closed-lost reasons. 

The compelling event: New product launch 

The offer: A short demo video or tutorial of the new product 

The CTA: A short conversation with your sales team to discover if the new product satisfies a requirement not previously met 

High-value content 

Content means different things to different people, and different types of content serve unique purposes. 

High-value or actionable content, such as original research or a how-to guide, constitutes a compelling offer for cold prospects. 

Not sure if your content is valuable enough to merit its own re-engagement campaign? Ask your internal subject matter experts (SMEs) if they would engage with the content of their own accord. 

Our internal resources serve as excellent gut checks for these types of things. 

The compelling event:A common challenge or a new tactic relevant to your prospect 

The offer: High-value content 

The CTA: It’s best not to jump straight to a CTA. Offer the content with no ask, then use marketing automation to see who in your campaign engaged with the content and follow up with them to see if they’re interested in revisiting the conversation. 

Free consult 

This one comes straight from the playbook of Jason Resnick, Founder of NurtureKit, an email marketing consultancy, and it has great potential to be leveraged by account executives at B2B software companies. 

After all, account executives work with tons of companies and have valuable insights into their clients’ strategies.

For example, Chili Piper’s account executives know the ins and outs of their customers’ inbound strategies, and they can leverage that wealth of knowledge to offer something valuable to prospective customers. 

The compelling event: A common challenge or a new tactic relevant to your prospect 

The offer: A free 15-20 minute consult or strategy session with an experienced account executive to share some success stories from existing customers.

It’s important to note this shouldn’t be a pitch directly related to your product. In fact, if you can share some success stories about larger initiatives for your existing customers, it will disarm your prospect and help them see you as a trusted advisor, rather than someone just trying to sell them something. 

If the conversation naturally leads to talking about your company’s product, then great. 

The CTA: Select time from a booking link 

“Two years ago, I offered a free consult for the next year to opportunities that had gone cold. It was 20 minutes, and it was no strings attached,” Jason shared. “I said, ‘If you have any questions, here's a booking link for 20 minutes, feel free to grab it anytime within the next 12 months.’ I sent that out to 13 people and nine of them took me up on it.”

“Three of those turned into clients. There were no strings attached, but through the course of the conversation, the deal was naturally revived. So three out of 13 people, that was a pretty good return on that little bit of time and investment that I made.”

A note on tech 

Whether you’re executing your re-engagement campaign through marketing or sales, there’s going to be some orchestration required on the back end. 

Usually, this entails you running an opportunity report in your CRM, segmenting that list to fit your campaign’s parameters, and then manually assigning leads or accounts to reps or importing the list to your marketing automation tool to execute the campaign. 

This is often a time-consuming process that requires collaboration across marketing, sales, and any operational resources available to the team. 

If you’re interested in learning how to power high-converting re-engagement campaigns without the fuss of manual lead assignments, check out Distro by Chili Piper.


About the author
Andrea Wunderlich

Andrea Wunderlich works in market intelligence and strategy. A former SDR, she understands first-hand the problems that Chili Piper solves — and the power of the Inbound Conversion movement. She lives in Atlanta with her husband and fur-kids.

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