Why I Lost a Fortune 500 Customer that Accounted for 30% of Our Revenue

About Author: David Aldridge is a Business Development Lead at Lohika, partnering high growth companies with elite engineering teams. In his off time, he climbs rocks, plays board games and watches movies far too seriously.

“We decided to go with your competitor.” - Words every sales person fears, dreads, loses sleep over.

I was dumbstruck. Jeri and I had been talking for several months. Like any enterprise deal, it had been an exercise in patience and hope.

I first met Jeri during our initial product demonstration. If we closed her organization, a Fortune 500 medical device company, it would be the biggest contract deal our scrappy little start-up by a factor of ten. So of course I went the extra mile.

We gave her an extended trial account for her to champion our product to her superiors. We then further extended that trial so that other audiences in the company could see it in action.

And then she went dark on me. Which, in hindsight, I should have seen as a sign.

But then without warning, I received a notification that her organization purchased our enterprise monthly package. We were jubilant. We’d just increased our annual revenue by 50% with one client.

After a week, I checked in with Jeri to make sure everything was copasetic on their end. It wasn’t. They’d discovered a bug, found new must-haves that our product didn’t have at the time, and generally had buyer’s remorse.


Short-Term Risk for Long-Term Gains

We offered to fully refund them their purchase, but still allow them access, and fix the bugs. A magnanimous gesture like that would have to help make them happy. That was the thinking, at any rate.

However, when I personally delivered the good news, Jeri did not react as I expected. She requested additional features and asked how soon we could deliver on those. Keep in mind, we’re an early stage start-up with a single-digit headcount. Moving quickly on features outside of our product roadmap would be challenging to say the least.

But the features she mentioned were features other clients had put on their wishlist as well, so we prioritized her needs.

A few weeks later, after the latest release was pushed, tested and approved, I reached back out to Jeri to schedule a demonstration of our new and improved product.

The demonstration went great, and Jeri indicated that her organization was ready to look at a monthly deal again.

Shortly thereafter, though, I heard the fateful words at the start of our story. Yep, the competitor ones.


What Happened to Our Fortune 500 Customer?

In our final conversation, Jeri confessed to me that her organization had originally purchased our product because of a feature that only came up briefly in our conversation. To be honest, it was a feature we hadn’t really invested that much in because our current customers didn’t use it often. Or at all. And in my defense, Jeri hadn’t emphasized its importance.

As a result, their organization chose the leader in our market segment. They were better funded, had a more mature product, and while it didn’t have that same feature, Jeri’s company felt it was a better match for their needs.



As salespeople, we’re taught to uncover all the layers of the onion. But sometimes, even if you think you’ve figured it out, you’re still looking for unknown unknowns.

Keep digging.

Or you too might receive those same words.