For True Customer Success, Upsell Conversations Can’t Wait

If you renew contracts annually, assuming a customer has been successful in the year prior to renewal, the chances are good that they’ll renew.

And if you bring up that add-on (that you should have orchestrated either when you signed them or early in the lifecycle of the last contract period), they should take the add-on, additional capacity, etc. being offered.

But sometimes a customer will say “sure, that add-on sounds great. Let’s add that. But you know what, I could’ve used that 9 months ago.


You should have offered them that add-on 9 months ago when they needed it; but you didn’t. Maybe you didn’t want to bother them. You didn’t want to “hurt trust” by trying to sell them something.

Maybe, as a policy, you just don’t talk about add-ons until renewal.

You better change that policy, Willy!

Remember, renewal and expansion are PART of the customer’s success.

The customer has to have been successful to date, and be on a positive Success Vector for there to be a valid expansion opportunity, but if those things are true and you’re not giving the customer what they need, when they need it, you’re not working to make them as successful as they could be.

That’s not Customer Success!

And what if — and this is a hypothetical — what if they bought that add-on 9 months ago… where would they be today? Might they have taken another upsell between then and now? Quite possibly.

You could have 3 or 5x’d the value of that account not by shoving product down the customer’s throat or by trying to meet some internal upsell quota, but by simply understanding where they are on their journey toward success and giving them what they need when they need it.

Now THAT is Customer Success!


Lincoln Murphy is a world-renowned Growth Architect, Consultant, Author, and Keynote Speaker. As founder of Sixteen Ventures — and previously leader of Customer Success Evangelism at Gainsight — he’s used Customer Success to drive growth across the entire customer lifecycle for more than 400 SaaS and enterprise software companies over the last decade.

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