That time we lost the sale
How we lost a slam-dunk prospect—and how you can avoid making the same mistake.
660 words • 4 minute read
Having the best product isn’t enough to win the sale. It helps, but it’s never the complete story. Fortunately at Pilot, the product and sales process are both good: we usually make a compelling case to the customer, and we get them on board.
This is a story about a time we didn’t.
The prospect in question was an early-stage startup that would have been a slam-dunk fit for Pilot. 100% our ideal customer profile. We would have been able to serve them super-well. And yet they chose to go with an alternative.
This happens so infrequently that it piques my interest when it occurs—I had to learn more. So I got in touch with the founder, who was generous enough to walk me through her decision-making process. After the call, I wrote an email to the team: we lost this sale, and we should have lost it.
Here’s the simple thing we missed on this particular sales interaction:
This process isn’t about you at all.
People want to buy products that feel like they were made for them, and are sold by people who get them.
In this particular case, we had an advantage right out of the gate: the founder had already heard great things about Pilot, was familiar with its reputation, and one of her investors had given us a hearty endorsement.
Said another way, this was ours to lose. And we did.
On our call, our rep launched into our then-standard talk track: Here’s Pilot, we work with thousands of startups, we have deep expertise, we can scale with you from pre-seed to Series D, and we have marquee investors. In short: “Here’s why Pilot is great.” Note the most common word here: “we”.
By contrast, the other provider didn’t talk about themselves at all. They asked about the founder’s business, and chimed in along the way with things like “Oh, we have this other client with that same business model. They made this one mistake on their tax forms, so be sure to double-check that.” The conversation was much more consultative: “Here’s what we think you need, and here are the pitfalls to avoid.”
At the end of the process, we were both comparably priced (they were a little more expensive), and the prospect selected the other vendor.
I asked the prospect where we went wrong, and what she said was: the Pilot sales process (and the Pilot sales rep) just felt too salesy. The theme of the conversation was, “This is why you should buy Pilot.” The other conversation made her feel like she was talking with a knowledgeable partner who was investing in a relationship.
Of course, the most frustrating thing here is that we work with literally thousands of companies like hers. Did we have a deep understanding of what her company’s needs were? Yes. Would we have been an excellent fit? Yes. But we didn’t communicate that deep understanding, and we instead spent time talking about ourselves. (We violated the classic creative writing rule: “Show, don’t tell.”)
I left this debrief call feeling energized, because I was sure that the prospect was 100% right. We didn’t lose because of the price. We didn’t lose because of the brand. We didn’t lose because of the featureset. We lost because we made the sales process about us rather than about the customer.
We made the prospect feel like we were there to sell, not to help. What the customer was really looking for was the reassurance that comes with having a trusted partner who cares about her business, understands her perspective, and gets what she’s looking for.
Effective salespersonship isn’t about presenting a sales deck with your product’s features, client logos, case studies, and a pricing table. It’s about actually solving a problem for your customer, and making clear that you’re here to be a partner in getting the problem solved.
It’s an obvious thing to say, but it’s amazing how easy it is to forget.