Selling to the C-Suite: Strategies for Executive-Level B2B Sales
- Matthew Earle
- Jul 1
- 5 min read
Updated: Aug 20
The Deal I Lost Twice: A Lesson in Assumed Influence and Missed Risk
Ten years ago, I lost the same deal. Twice.
Just think about that for a minute. How many seasoned sales leaders can say they lost the same deal twice?
This wasn’t a typical sales opportunity. It was a channel tracking solution for a multi-billion-pound manufacturer: a big name, high visibility, and the kind of logo that transforms your credibility overnight. They were forward-thinking, and looking for a strategic partner to change how they operated across multiple markets.
I had been working with my champion in their business for 18 months. We identified a clear competitive edge and built a solution using tools already in our kit that would change the game for them.
Because of this exciting premise, we had been introduced to senior stakeholders in other parts of their business, and were already in talks with other divisions on how we could roll this out in their markets. Had we landed this, it would have opened doors across the entire organisation. The kind of deal that turns into a long-term strategic partnership.
The First Loss
We had developed the proposal together. I had met the CMO and presented to him on the wonders of our solution. He seemed very excited. I met multiple people and was led to believe were all decision makers (or at least influencers).
My SLT were buzzing. This was the deal.
I was getting daily phone calls asking for updates, how this would impact our forecast, how we would compensate the sales team working on the deal. It had gone all the way up to the group MD and even he had started emailing me, offering support if needed. I was fine. I had this.
The first warning sign? I was asked to present to a group of five. I’d only met one of them before. But I convinced myself that this was just the procurement process in action - a box to be ticked. After all I had been told that it was a slam-dunk.
The first time we lost the deal, I was gutted and felt personally aggrieved. I had done everything right. I hadn’t pitched too early. I’d spent months understanding the business, the requirements, the ROI. I had a champion pushing us hard. We had a name in our industry.
I had built a strong relationship with someone I believed was our internal champion, someone who really understood the value of what we were offering.
He’d helped navigate procurement, brought the right people into early conversations, and seemed to have the influence we needed to move things forward.
I was confident.
Then came the text.
My ‘champion’ messaged to say he thought they’d made the wrong call. Said he’d try to push back internally. I appreciated the honesty, but it didn’t help.
I was confused. Had they delayed the decision? Changed scope? Baulked at the price? So I called him frantically.
At the last minute another vender had entered the fray and they had decided to select them instead.
I was devastated. In my head I had already spent the commission, was thinking about how to scale the sales team, and was preparing for the hearty congratulations from our SLT.
Later that day procurement sent the official “thanks but no thanks” email. I forwarded it to the SLT and waited for the requisite bollocking. It did not come, instead I got pity and commiserations.
It hit really hard. Not just because of the size of the deal, but because I knew the work we’d done was strong. And we'd already started scoping opportunities with other business units. I felt like we’d just been cut off at the knees.
But what happened next made it worse.
The Second Shot and the Second Loss
A month later, I got a call from my 'champion'.
The vendor they’d chosen had failed due diligence. They wanted to re-enter negotiations. I saw it as a second chance. Redemption! It was a sales miracle from the selling gods!
I excitedly emailed the SLT. Within seconds, the MD called me asking what I needed to get this over the line.
I quickly pulled together a new commercial offer. Built a roadmap. Even added a few discounts to address what I thought were their pricing concerns.
But in my rush to re-engage, I repeated every mistake I’d made the first time.
I didn’t insist on meeting the wider buying group.
I didn’t uncover what their real concerns were about working with us.
I assumed we were the only horse left. That all they needed was reassurance, and a discount to seal the deal.
A week later, I got the final call. Another rejection. Another email to the SLT. More silence.
This time, I angrily asked for a debrief.
And what I heard floored me: “We saw your solution as the riskier option. The other vendor had financial red flags, sure but at least they had a proven track record in our market.”
They didn’t lose confidence in the product. They lost confidence in the fit.
And I hadn’t given them enough to counter that perception.
What I Got Wrong and What I Learned
Looking back, the problem wasn’t the product.
It was my qualification. Or lack of it.
I’d made four critical mistakes:
Assumed I had a champion.
He liked us, but he didn’t have the influence I needed. I didn’t validate his power in the decision-making process. He was in it for the personal kudos and told me everything I wanted to hear, but he did not have the authority or access to power that I had assumed. I had not validated this and blindly trusted everything he said.
Failed to map the decision-makers.
I relied on one 'trusted' voice to carry the message. I should’ve pushed to meet the rest of the group and understand their concerns directly. Why didn't I? Its because I believed I had all the access and influence I needed. My confirmation bias told me I didn't need to.
Didn’t dig deep enough into the risks.
I thought price was the key barrier and the thing most likely to kill the deal. In reality, it was trust. In the debrief, I asked for their top three vendor selection criteria. Price didn’t make the list. They weren’t convinced we were the safer bet and I didn’t surface that early enough to counter.
Didn’t fully quantify the problem.
Our solution was good. But they didn’t see the urgency. I hadn’t done enough to build the case that this was a must-fix issue. It felt more like a nice-to-have. A differentiator that over time would make them the easier manufacturer to do business with. I had not dug down to the quantifiable risks of inaction. The ROI was based on future uplift in sales and not the pain points of now and in the future.
Why PROBLEM Exists
That experience shaped the way I sell and the way I coach others. From that moment on, I stopped trusting my instincts, self-declared “champions,” or second-hand opinions. I learnt to be sceptical, to qualify in black and white and validate, validate, validate.
It’s why I built the PROBLEM qualification framework.
Because most sellers are too quick to label a contact a ‘champion’ or to accept surface-level pain as the real driver.
We miss things.
We assume influence.
We skip hard conversations about risk.
And we hope urgency will appear by magic.
The PROBLEM qualification framework doesn’t.
If you're not qualifying properly, you're not selling, you're gambling. And trust me, it's not a nice place to be.
The cost of that gamble? In my case, it was a partnership that could’ve transformed our business. And a lesson I won’t forget.
Want to avoid making the same mistakes?
Take a look at how the PROBLEM framework helps teams uncover the truth early, manage internal risk, and qualify deals that actually close.
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