The Upsell Sequence that 4x’ed Conversions on Our Latest Product Launch

Posted by Pat Henseler in B2B Lead Generation & Sales Insights

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We've tested numerous upsell strategies, software and services in our purchase process, and the strategy from our recent product launch generated 4 x the amount of sales. In this blog post we'll share with you the entire playbook we used. 


And if you're interested in more strategies to automate your sales process with email today, be sure to sign up for our Create Your Sales Automation Bootcamp today!

This likely isn’t the first blog post you’ve ever read about upsells.

They are a major part of most sales processes in place today. In this post specifically, I wanted to share an upsell sequence we implemented on a recent launch that got an especially good return.

Many people put a lot of emphasis on upsells at the time of checkout.

You’re probably familiar with something be offered to add to your purchase. Warranty plans on tech hardware or extended service plans on vehicles for instance:

​Maybe those offers caught your eye at checkout and maybe they didn’t.

But what we’ve found is that often times the whirlwind of emotions your client is having at the completion of a sale (‘I can’t wait to get started!’ ‘This is going to change my life!’ ‘How am I going to tell my wife about this purchase?’ ;-)) can often lead them to ignore the upsell without giving it much thought, or even get frustrated by it.

That’s why having a one-and-done approach with your upsells can leave a lot of opportunity on the table.

So to avoid that, you want to make sure that you present the offer again, but it has to be done in the right way.


  1. You want it to tie into your main offer.
  2. You want it to give a personal reason why you are bringing this back up to them.
  3. You want it to get results.

In this post I’m going to lay out for you how we handled our upsell email sequence to account for all three items above, instead of just relying on our customers to take it at the time of checkout.

The Sequence

24 hours later the people who didn’t either reply say “No thanks!”, book a call with our team, or purchase the upsell, received this follow-up message.

Tie Your Upsell to Your Main Offer


This might sound like a given.

But it’s step 1 to having a successful upsell offer.

You need to connect the dots for your customers to explain why this is a valuable addition to their original purchase.

How does it help them get more done? Or get things done quicker? Or scale how they will use your product or service to the next level?

In the case study we are reviewing the product we were selling is The Appointment Generator, an online training and coaching program that teaches our customers how to use LinkedIn and email to book appointments with their ideal clients.

The upsell offer is that we’ll have our agency team set-up the foundation of their Appointment Generator campaign and go out and get them a database of connections that they can use in their messaging campaigns.

We make a case in our video sales letter for how this will take a lot of the heavy lifting off their shoulders and get everything started for them so that they have a huge head start on the work that they need to do.

It helps that the service we are promoting isn’t something that we sell as a standalone. The only place it would make sense is for customers that have the training and coaching to complete the process., but maybe not the man hours or team to get the system set up for them.

Give a Personal Reason Why


Most funnels and upsell offers feel cold and impersonal.

It’s got the feeling of ‘Squeeze as much out of your customer as you can.’ But it doesn’t have to be that way.

If your upsell provides real value, then it shouldn’t feel cold or pushy. It should feel more like a helpful suggestion than anything else.

This might be the most important part of what worked well with this particular upsell sequence.

A typical one-click upsell may get some takers, but it’s hard to make a checkbox or a video that starts automatically on purchase feel personal. Like an individual recommendation.

The only way you do that is with personal outreach.

Now, that could be done with a phone call.

Or in our case, we sent a personal email post-purchase to those that hadn’t taken the original checkout upsell offer.

This wasn’t sent as a typical autoresponder with funky formatting and through some 3rd-party email server.

It was sent through a direct email account integration.

We utilized our software Connect 365 to deliver these messages so that for our recipients it would look just like an email handwritten for them.

For the first message, we sent this out 2-3 hours after the initial purchase to anybody that didn’t take the upsell immediately.

We do this because many people complete their purchase and then exit out of the next screen to get back to their work or the webinar they heard about The Appointment Generator on, or because many of these people have never seen the upsell offer at all. Other times, we’ve found that users tell us there was a technical issue and they never had a chance to even purchase the add-on.

Either way, we make this email feel unique to their purchase by telling them how excited we are and reinforcing their previous decision.

And again, as you can see from the screenshot, it looks like an email that was hand-written for each individual.

It doesn’t have some impersonal formatting like you may be familiar with for big consumer brands or B2B newsletters.

Or weird headers and images like this.

While emails like that certainly have their place in a bigger marketing plan, they aren't fooling anyone into believing this was personally written just for me.


Rather the approach that worked best for us was just simple, direct, relevant, and looks personal to the recipient.

Get Results with It


Ultimately, the strategy and reasoning behind all this wouldn’t matter if it didn’t get results - in this case, an increase in sales or building a better relationship between our company and our customers.

The sales part itself was a significant boost.

We saw orders of this upsell increase 410% simply from the follow-up offer after the initial purchase.

In previous years we were hoping to add just a couple additional sales through typical autoresponders with our big CRM.

But by strengthening the offer to integrate seamlessly with the main purchase and approaching them in a personal way with the help of Connect 365, we were able to generate a significant boost to our bottom-line AND help more of our customers have the best possible chance of success with their marketing campaigns.

A win-win if I’ve ever seen one.

Curious how you can utilize Connect 365 and email to generate more sales opportunities for you and your team?

Get more information on the process below:


Automate This Strategy With Connect 365


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