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What to keep in mind when selling to your first upmarket customer

Be wary of ‘happy ears’ with upmarket customers

Senior Director of Sales, Intercom

David Katz


Main illustration: Uberpup

There’s a classic response people have when talking to larger companies – I call it happy ears.

It’s incredibly easy to be overly optimistic when you see a sexy new logo walk in the door. The thing you forget is that at large organizations, there are lots of people there who are constantly evaluating technology and looking for ways to use those new tools to help them stand out or leverage a proposal to negotiate better terms with their current vendor. But out of all these evaluations, very few purchases are actually made.

“The reality is that you should walk away from 99% of these early conversations with larger customers”

As a sales leader, you have to be very dubious of this situation. The reality is that you should walk away from 99% of these early conversations with larger customers. If you can’t get the stakeholders on the other end to give you straightforward answers, agree to a mutual evaluation plan or meet shared deadlines, then it’s time to walk away. The absolute worst thing you can do is waste your time or theirs.

Evaluating the needs of upmarket customers

Even if these early conversations do go well, inevitably there will be things larger customers ask for that you simply don’t have yet. There are four critical questions you can ask to get ahead of their needs from the get-go:

  1. What are their must-haves from a current functionality perspective? And why? Oftentimes, this will be things like administrative capabilities, reporting functionality, security protocols and integrations or APIs.
  2. What are their must-haves from a future functionality perspective? And why?
  3. What are the nice-to-haves they hope will come in the not too distant future? And why?
  4. Lastly, what are your current differentiators that get them really excited about taking a bet on you and bringing your tool into their tech stack? And why?

Don’t be afraid to hear “no”

If you don’t have it, you’re not good at it and the plan isn’t for you ever to work on it, be honest with your stakeholders. The right early upmarket customer will ultimately be sold on the vision you paint for them, not on a checklist of features.

“The right early upmarket customer will be sold on the vision you paint for them, not on a checklist”

People evaluating software vendors, especially people evaluating lots of them, appreciate transparency. It means you’ll hear “no” more often than not, but getting to “no” faster is preferable. And when the time is right down the road, those same people will also remember you for it.

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