On Lost Deals

Something that is often not shared enough in founder circles is that for every enterprise deal you win, there is another equally perfect one you lose. For some reason, you're just not able to get it over the line.

Losing deals is a fact of life, but it's never easy, especially as an early-stage founder. Most of us are new to enterprise sales (probably new to sales in general), and selling something that is our baby. It is truly heartbreaking to lose a great deal.

Enterprise sales feels like American Ninja Warrior. You get through the initial hurdles: finding the right company, the right team, one that is legitimately, deeply experiencing the pain you built an entire company to solve.

When you find those teams, it doesn’t feel like sales. It feels like helping another human achieve their goals. You get to reduce their pain and make their life better, and you are uniquely positioned to help. That feeling is incredible.

Yet sometimes, even then, the deal doesn’t go as planned.

Recently, I lost a deal that shook me to my core. Everything was looking great - we had won a bake-off against other vendors, the budget was secured, and we made it through procurement without hiccups. Then, during the final rounds of MSA negotiation, it fell apart.

It turns out, what we thought was an administrative approval ("just a box to check") from C-suite leadership was actually a much larger hurdle.

Deals fall apart for many reasons. Some are your fault. Some are not. Some are not technically your fault but could have been anticipated better.

Misalignment (aka Insufficient Discovery)

The first big place where things fall apart is misalignment.

You think you understand what the team wants. They provide requirements. You see how you fit. But especially in competitive situations, especially when multiple solutions are being evaluated in parallel, it’s incredibly important to show that you truly get them.

Not forcing them into your way of working.
Not autocompleting in your own brain what you think they want.
Not assuming.

You have to really, deeply understand what they are building and why. You have to shape the proof of value and the success criteria to be fully and explicitly aligned with what they care about.

For us, when we lose at the proof of value stage, it is often because we didn’t do enough discovery upfront. We didn’t fully understand what they were building. We didn’t align tightly enough on what success actually meant to them.

Leadership Buy-In

The second major failure point is not securing leadership approvals (whether for budget, business case approval, or final sign-off) because you didn't prospect high enough in the organization.

At Amazon, I was an IC engineer. I’m very comfortable talking to ICs. I’m comfortable with managers and managers’ managers. But as you go higher into senior leadership, priorities and perspectives change. They are juggling a completely different set of constraints.

And those senior leaders are the ones with real power.

Even if everyone below them is excited. Even if your champion loves you. Even if the team is ready to buy, without executive buy-in, it doesn’t matter.

That most recent lost deal was particularly painful because I thought I had done enough. I had prospected through what I believed were decision-makers. I was speaking with someone who had authority to make the purchasing decision, and the budget to do so, but still needed C-suite sign-off.

I never spoke to the C-suite executive.
I never asked for an introduction.
I never reached out.
I assumed the approval was a rubber stamp. A paperwork formality. I assumed my champion would advocate for us when we weren’t in the room.

I was wrong.

Enterprise sales is not just about finding a great fit and delivering value. It is about alignment at every layer of the organization, especially the layers that can kill the deal.

Losing deals hurts, especially when you know you could have helped. Especially when you believe deeply in what you built.

So now what

The best solace is knowing that now you know. Startups are a game of experimentation and learning, and sometimes the best lessons are the most painful. Take a minute and mourn the loss, but then get back out there, and do better than you did last time.

And, life is long. If that company is still experiencing these problems in 6 months, or a year, we'll be here. I think about the long game, and continue to build those relationships. As a sales leader once told me "doing what's right for your people always comes around."