Your customer signed up with particular objectives in mind but somewhere along the way they might have forgotten.

If they haven’t reached their desired result, then brainstorm a few ideas to help them achieve their goals with their existing investment.

This makes the conversation have more sense because it invokes trust and lets them know you care enough to not let their investment go to waste.

If your customer purchased your product to achieve a particular goal “A” do but they’re currently only using 2 out of 10 of the main features needed to achieve the goal “A”, use your customer success software to compare actions between your customer and users with similar attributes.

You’re already using features 1 and 2. When customers within your same vertical also use feature 3, they’re able to achieve “A” just by expanding their understanding of how to use our product.

Show them a quick win and they’ll be more likely to pick that phone up next time you give them a call.

It's often difficult and risky to initiate an upsell conversation with a costumer out of the blue. It can be inconvenient and could cause in a loss of trust.

Instead of this, incorporate an upsell conversation into a current commercial engagement like a project renewal or an expansion. This way it won't feel forced or awkward.