How to Create an Email Campaign that Inspires Service Upsells

Alex Sobal
Posted by Alex Sobal on June 29, 2016


While you could categorize a lot of different marketing tactics as “hit or miss,” email marketing has to be one of the most hit-or-miss strategies. After all, you really only get a few words to use as persuasion to open your emails, and if that doesn’t work, you’re basically S.O.L.

To get some better insights on what it takes to create a successful email campaign for, I asked our President and CEO (Chief Email Officer), Greg Linnemanstons, more about the email planning process and using email to maximize customer upsell opportunities. 

According to him, a successful email marketing campaign for existing customers can be broken down into 7 steps:

Step 1: Identify Upsell Opportunity

Because email marketing is one of the most hit or miss marketing tactics, you always need to have a well thought-out plan heading into your campaigns. People aren’t going to waste time with email they deem to be junk, so you need to entice them with an offer they can’t refuse. How do you do that? By talking to your sales reps, your customer service, your field reps, and even your customers themselves to identify the biggest needs of your customers and figure out what makes them tick. 

Ask your sales reps if there’s a trend with customers who upgrade their service. Are they doing it for a particular reason? Likewise, don’t forget to ask what reasons customers give for NOT buying/upgrading. Knowing what’s holding them back could help you create a better offer for your email campaign. For example, if you discover the majority of your customers are hesitant to upgrade because they’re not sure if the added features are worth the added monthly price, try sending out an exclusive email offer with a free or discounted 3-month trial. 

Step 2: Identify Upsell Targets

This step will most likely intersect with Step 1, but once you identify an upsell opportunity, you need to identify a list of targets to send the email to. While you’re talking to your sales reps about your customers’ pain points, also ask them which ones would be prime candidates for an upsell opportunity.

For example, let’s say you provide CRM systems for SMBs, and you want to persuade your customers to upgrade from the basic level to the “Franchise” level. After talking to your sales reps, you discover that most customers who upgrade do so because they’ve reached their maximum number of managed contacts. If your basic level of service offers management of 500 contacts and your Franchise level offers management of 2,500 contacts, create an email list of customers at the basic level with over 350 managed contacts, as they’ll be prime candidates to upgrade.

The more targeted and personalized you get with your recipients, the better you can address their pain points and the more success you’ll have upselling to address those needs.

Step 3: Promote the Offer as Helpful

Once you have an upsell in mind with the right audience, the next thing you need to do is make sure they have a reason to buy into the opportunity you're presenting. One way you can do this without coming off as sales-y, is by positioning the upsell as something that will help them, as opposed to just an upgraded service.

For example, using the CRM scenario from Step 2, if you warn customers who are approaching their contact limit that it might be a good time for them to upgrade, you’re really just helping them stay up to pace with their business, as opposed to pushing an upgrade on them right away. The Dropbox email below is also a good example of this.


Another way you can be less sales-y with your upsell opportunity is by positioning it as something other customers have also been interested in, or as a complement to their previous purchase. I’m sure you’ve seen the recommendations on and other websites, for example, and a personalized email saying “Hey [First Name], if you like this, you might like this” is much more genuine than one that just implies “Buy this!” 


Step 4: Come Up With a Good Subject Line 

Having a good subject line is a key element of any email campaign, but it's even more critical when you're trying to inspire upgrade purchases. Ideally, your subject line should be something concise, punchy, and attention-grabbing, but try not to lead with anything sales-y like “Upgrade Today!”

Instead, you should invoke that tone of helpfulness in your subject line, and try for something more like “Look out! You’ve almost reached your contact limit!”

If you do end up choosing a promotional message, make it an attention-grabbing line they can’t resist, like “Try Franchise Level for only 99 cents/month!” Whatever route you end up taking, you should try to come up with several usable subject line ideas (which, of course, leads me to the Step 5).

Step 5: A/B Test Your Emails 

Because email campaigns can be hit or miss depending on lots of factors, you should test as much as possible. Thankfully, with today’s technology, it’s easy to A/B test multiple email versions, subject lines, pictures, CTAs, etc., and figure out which email has the best chance to inspire the most upsells. Make sure you create a few different versions of your emails and subject lines, and send them to a sample of your list. See which emails earn the highest open rates, the most clicks, and most conversions, and combine them all into one.

Step 6: Have Automation Workflows Ready

A lot of people might think an email campaign ends once you hit send, but there’s still a lot you can do after the fact. One thing you should always do is set up email nurturing workflows based on different actions people take with your initial upsell email. For example, if someone converts, make sure they’re put into a workflow introducing the new features to them.

Maybe they’re not ready to upgrade, but they check a box saying they want to stay updated about future deals and upgrade opportunities. Do you have an email nurturing campaign set up for that? There’s a lot you can do to maintain contact once the initial email is sent.

Step 7: Analyze the Results

A few days after the email’s been sent and your list has had time to check their emails, analyze the results of your campaign and take note of what worked well and what didn’t. Look at things like open rates, click through rates, and the number of conversions to see how well it performed, and make notes of these things to increase the success of your future emails.

There’s a lot that can be said about email marketing in 2016. On one hand, people are getting better at ignoring spammy, irrelevant emails, but on the other hand, marketing software like HubSpot is making it easier for companies to send personalized, relevant emails to their customers. It’s a dual-edged sword really, but you’ll win a lot more of your email battles if you properly research your audience beforehand, and position your offers in a way that truly help your customers.

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Topics: Marketing Automation, Email marketing

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