Ending The "Should Customer Success Manage Upsells?" Debate

Go to any Customer Success talk or meetup, and inevitably the question will come up of whether or not Customer Success should be responsible for upsells. From staunch Customer Success advocates, you’ll most likely hear a resounding “No!” and from operational leaders, sales leaders, and C-suite, you’ll most likely hear a resounding “Yes!”

So what is the reason this debate, which has been going on for years now, remains unresolved?

The answer is: we’re not speaking the same language.


If tomorrow you decided to start learning German, you would most likely begin by learning some German words, and then looking up what they mean in English.

Die Frau = The woman

Der Mann = The man

Das Auto = The car

You’re not learning what “Das Auto” is as a concept in German, you’re simply learning a new word and attaching a meaning that already makes sense to you: “The car.”

The same thing has been happening with Customer Success and Sales.

The language of Customer Success consists of words like: relationship-building, coaching, support, and strategic planning.

The language of Sales consists of words like: selling, upselling, renewing, and expanding.

And in order to allow these two critical teams to work together, we’ve tried to translate the language of Customer Success into the language of Sales.

The problem is, as we’ve seen throughout history, that language is powerful, and changing the language used affects behaviour.

For example, one could say that “building strong relationships will lead to upsells, so for simplicity, we should just say that Customer Success is responsible for upsells.” While this statement is technically true, telling a Customer Success team that they are responsible for “upsells” versus telling a team they are responsible for “relationship-building” will yield extremely different results.

This leads to a second problem: how do you go to your CEO and say “I don’t want to be compensated based on upsells, I want to be compensated on the strength of the relationships I build with my customers.”? (a conversation that will probably end very quickly)

This is where the real work needs to be done. Instead of wasting time, going back and forth on this ‘upsells’ issue, Customer Success leaders need to be devoting this time and energy to determining how to communicate the real value of what we do. Instead of trying to speak a different language, let’s help those who are not in Customer Success to understand ours.

How can we assign a dollar value to the strength of a relationship? How can we conclusively draw a line connecting strong coaching to speed of expansion? How can we show that if there is a strategic long-term plan in place, that the customer is X times more likely to renew?

Yes, it would be much easier to throw in the towel and just say “screw it, we’ll manage upsells—we understand it, Sales understands it, Leadership understands it…” but do you know who ends up losing in that scenario? The customer.

We owe it to our current and future customers to put in the work now, so that we can focus on helping them to do amazing things, rather than trying to squeeze every drop we can out of them to hit our upsell quotas.

It’s time we stop trying to translate what we do into languages people already know, and we instead begin to teach them a new one.


Next Steps (if you’re feeling inventive)

  1. Create methods for measuring the strength of relationships, the quality of the coaching provided, and the excitement/buy-in for a long-term strategic plan.

  2. Using these new measures, determine what the dollar value is for each data point. If relationship strength is 10 out of 10, what is the average upsell percentage? 50% of the original contract? 100%? If relationship strength is 5 out of 10, what is the likelihood of churn? How much revenue is at stake now, given that the relationship is weak?

  3. Create systems to automatically track the metrics, assign values to them, and project forward.

  4. Once validated, integrate these systems into tech stacks.

Do you have thoughts on these steps? Have other questions or comments? Email me at ben@csinfocus.com.

Ben Winn