What I learned from losing a $500k deal

In the next two minutes you’ll walk away with one tip that can save you from losing deals in the last minute.

I was ready to call it a day when I got an email saying they weren’t moving forward with us. A 500k ARR deal lost at the 11th month. If we were going to lose, it should’ve happened much sooner. But I made a mistake at month 6. A mistake I didn’t notice at the time, but one I wouldn’t forget anytime soon.

Let’s rewind to September 2020

A VC cold emailed our CEO which led to an intro to the dev team of a Fortune500 company. There was a clear need and timing was just right - it was a top priority project and scoping was already underway.

We were talking to lead engineers who’ve been with the company for 10 years. They knew the pain they needed to solve to deliver impact and when they need to deliver it by. They knew everyone who’d need to get involved throughout the project. They knew what they’d need to validate and present internally to get approvals.

Any sales rep would tell you this is a dream come true. All I need to do is to make sure the team has everything laid out on a silver platter so they can do what they do best. And I still lost. Why?

I got overconfident.

Building the business case took 8 months, but we finally made it through most of the red tape. Security review done, tech evaluation done, the dev team couldn’t wait to get started, and we just started with Procurement and Legal. By this time we’d met 8-10 stakeholders from different departments and knew how they were going to contribute to the project.

If you were reviewing the project following MEDDPICC you’d say everything looks sound. What reason did I have not to be confident?

The thing is, discovery isn’t a stage. It starts when you start researching an Account and continues for as long as you’re working with the Customer. But instead of constantly looking for reasons this deal could fall through I was focused on pressing on the Critical Event and Cost of Inaction to keep the ball rolling.

We’re now at month 6 and a new VP of Engineering joined the company at the beginning of the year. I know because a month later my main contact told me about it. But since I was talking with people who’ve been with the org for 10+ years, people who were championing our product, I thought we had this in the bag. I never considered the need to talk to the new VP 1:1. And that’s why I lost.

The next 3 months were like pulling teeth.

The legal review led by the Procurement team was dragging on slow - meeting up every two weeks and barely making progress.

When I lost the deal early August we were almost 2 months over the desired go-live and the new VP needed to make the call. They couldn’t afford any more delays on the project. They decided to build on top of their current solution.

It felt like a punch in the gut. A cold shower reminding me that no matter how experienced you are you can still mess up royally.

And although they made it clear that we can resume the talks next year, that this isn’t forever just a goodbye for now, I learned a lesson I wouldn’t forget anytime soon.

So what would I do differently that you can start using today?

1. Build strong Champions (plural) and don’t confuse a Coach for a Champion. Champions have Information around the project and priorities, an Incentive to choose you, and have Influence inside the org. Coaches only have the first two.
2. Set up alerts for job changes inside the Accounts you’re working so anytime a potential stakeholder joins, leaves, or gets promoted, you can keep the deal safe. Anytime someone new joins the convo, grab a 1:1 time. No matter if they’re a VP or front-line employee. When it comes to enterprise deals you never know what impact they can have on the deal.
3. Multi-thread constantly. The last thing you want is to lose deals due to hidden stakeholders or not knowing how a given person truly feels about the project and how it should be done.

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