3 steps to creating upsell opportunities

In today’s issue, I’m going to share a simple, 3-steps play I recently used to get a 60% reply rate, and a 67% meeting rate.

If you can replicate this play, you’ll be able to start key conversations with existing customers, and identify upsell opportunities.

Unfortunately, most SDRs focus on generating net new business, and they forget that easy opportunities can easily be found (and closed) with existing customers.

In 2023, upsells and cross-sells will help you reach your targets.

But without a solid expansion prospecting play, two challenges arise:

Challenge #1: You focus on booking tough meetings: you’re only trying to start conversations with prospects who never heard about you.

Challenge #2: You miss on easy opportunities: you’re not able to get valuable conversations with customers who already know about you.

You can overcome these challenges by creating upsell opportunities.

Here is a simple play I tried last week, and I got 3 replies and 2 meetings booked out of it:

Step 1: Identified 5 customers I worked with

In 2022, I’ve been selling all kinds of training and coaching to various types of buyers. A lot of them have purchased an online course, or a coaching session for their reps.

I’ve compiled a list of buyers, with the service they purchased, and the values of different products they bought.

If they bought more than one product, they are at the top of my list. I’ve also included the customers who had great outcomes.

It took me around 30 minutes to come up with a solid list, and I ended up selecting the top 5.

Step 2: Sent them a thank you email

Now that I knew who I wanted to reach out to, I started crafting a thank you email. I focused on the training they purchased, and the outcome they got out of it.

Here’s an example:

“John, how are you doing?

2 things:

1. I’ve been reviewing people I worked with in 2022 and I wanted to say thank you for having your reps join the program! Mary mentioned she cut her demo calls in half and managed to qualify opportunities faster.”

Step 3: Searched for problems

In the second part of the email, I asked if my customer knew about people who were struggling to reach their targets. I also teased a potential resource to help them with this specific issue.

Here’s an example:

“2. I’d be curious to know if you know of people who are having challenges reaching their targets. I may have something for them.

Thanks again for working with me!”

The results

After sending 5 emails, 3 customers replied (60% reply rate), and 2 booked a meeting with me (67% meeting rate). I was able to generate one opportunity, and I’m in conversations with the last customer who replied to book a meeting.

It’s also interesting to note that two customers asked for help with their business (upsell and cross-sell), but another one introduced me to people he knew with similar problems as them. That’s why I didn’t ask for introductions, but asked for problems.

And these are my 3 steps to creating upsell opportunities.


  • Step 1: Identify 5 customers you work with

  • Step 2: Send them a thank you email

  • Step 3: Search for problems



P.S. When you’re ready, here are 4 ways I can help you.
  1. Build your outbound prospecting system from scratch here (230+ students)
  2. Write cold messages that get a 38% reply rate and 27% meeting rate here (40+)
  3. Book me 1:1 or for your team here
  4. (NEW!) Sponsor my newsletter & get 3K+ eyeballs on your ad!

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