Looking back: April 2026
I’ve told versions of this story to a lot of people I’ve mentored. It’s one of the cleanest lessons I’ve ever learned in enterprise selling, and it cost enough that I remember the details more than a decade later.
The Setup
The deal was with a large telecommunications carrier. The champion was the CIO — not just my champion, my lead champion. The kind of executive sponsor every enterprise seller hopes for. She understood the technology, had authority over the decision, and had personally advocated for our solution against internal skepticism.
We were nine months into a 12-month cycle. The deal was worth low seven figures. Legal was engaged. Procurement had the redlines. I’d forecasted the close for the following quarter, and the number was good enough that it was going to earn my team president’s club.
Then the CIO got promoted.
Not to a better role at the same carrier — to a different business unit. A different market segment, a different portfolio, a different buying authority. She wasn’t leaving the company. She was moving to a role that had no visibility into, or authority over, the deal she’d been championing.
What Happened Next
Her replacement walked in on a Monday. The handover was less than a week. Her new boss introduced her to the vendors she was inheriting as part of the buying portfolio — including us.
She was professional. She took the meeting. She asked good questions. And then she made clear that she wanted to take the next 60 days to evaluate all the open vendor relationships and make her own assessment before moving forward on any of them.
Sixty days became ninety. Ninety became one hundred and twenty. By the time she was ready to move, the internal budget timing had shifted, the original business case had to be rebuilt with her name on it, and the organizational momentum we’d built over nine months was effectively reset to zero.
The deal didn’t die. It closed — nine months later, at 60% of the original scope, because by the time the new CIO was comfortable, the business conditions had shifted.
What I Got Wrong
I had multi-threaded the deal somewhat. I’d built relationships with the CIO’s direct reports, with procurement, with the architecture team. What I had not done — and this is the specific failure that cost me a year — is build a relationship with the CIO’s peer executives or her boss.
My champion was strong. But she was single-threaded on her own authority. When she moved, her authority moved with her, and nobody above her had a personal investment in the deal.
If I’d invested in one relationship at her boss’s level — a casual but consistent relationship over the nine-month cycle — the transition would have played out differently. The boss would have vouched for the deal to the new CIO. The new CIO would have inherited a semi-endorsed relationship instead of a blank-slate evaluation.
I didn’t build that relationship because I didn’t see the need. The deal was moving. The CIO was on board. Why burn political capital to get time with her boss when everything was going well?
The reason why is exactly the scenario that played out. Deals don’t die when they’re going well. They die when the conditions change. And the conditions always change.
The Principle I Now Apply
In every enterprise deal I’m in now — or that I coach someone through — I try to make sure there’s one relationship above the level of the primary champion. Not deep. Not intrusive. Just enough of a personal connection that if the champion moves, promotes, or leaves, there’s someone else in the organization who remembers the deal, thinks favorably of us, and would advocate at the executive level.
This relationship often takes a while to build. Executives above the buying authority don’t have time for vendors who aren’t specifically relevant. So the relationship has to be built on something other than the current deal — shared industry interests, introductions to other executives, a perspective you can bring to their strategic questions.
It’s slow and inefficient in the short term. It pays the moment your champion moves, which is more often than most sellers expect.
I don’t often tell this story at scale because it’s specific and personal. But I think about it every time I look at a pipeline. Every single-threaded deal is one job change away from dead. I learned it in telecom. The lesson never stops being relevant.