The short version
Because I saw that this major Canadian retailer was already asking whether all of its marketing technology should move, I knew a pilot of one use case was too small an answer. I chose to let the pilot prove the platform while I built the case to replace the incumbent marketing cloud, and to co-sell with Microsoft so the customer could put the deal toward commitments it already had. That led to an 8-figure, four-year deal in about twelve months, the largest retail deal in my business that fiscal year, and put me at 173% of quota year to date, #1 on my team.
The obvious deal vs. the deal I built
- The obvious deal: a small pilot of one use case, running beside the marketing cloud the customer already had.
- The deal I built: a four-year replacement of the customer’s marketing technology, with one platform running customer communications across every channel, and a plan finance could approve.
The pilot was the easy path, and the customer was comfortable with it. The business was heavily invested in the incumbent and did not want to change. A pilot on its own would have kept two systems running and pushed the real decision out.
This deal followed the four milestones of my Strategic Deal Roadmap: early alignment, go wide then deep, a defendable business case, and executive commitment with a team that can deliver.
Milestone 1: Early alignment
I saw a customer with years of investment in its incumbent marketing cloud and no wish to switch. I was given the account as our #1 strategic account in Canada, and it had just started a pilot. Some leaders were already asking whether all of their marketing technology should move.
I decided to treat the pilot as the first step of a bigger decision, not as the deal.
Because a customer that is willing to ask the big question has already opened the door. My job was to help them answer it.
Milestone 2: Go wide, then deep
I saw the pilot start with a single use case. As it ran, the scope grew to omni-channel communications across every channel the customer used.
I decided to bring Microsoft in as a co-sell partner and offer the deal through the Microsoft marketplace, so the customer could put it toward its existing Microsoft commitments.
Because a big switch is easier to approve when it fits how the customer already buys. The money was already committed. The question became where to use it.
Milestone 3: Make the business case defendable
I saw that a switch this size would be decided by finance, not by the marketing team. The proposal and forecast ran to hundreds of rows and columns of volumes and pricing over a four-year term.
I decided to build the case around value, phasing and risk, so finance could see how the customer would move off the old platform in stages.
Because finance leadership is not approving software. They are approving a plan they can defend.
Milestone 4: Executive commitment, and a team that can deliver
I saw that it all came down to one meeting with the senior finance leader. The night before, the customer’s senior technology leader, who was presenting, messaged me with questions on the proposal and the volume numbers.
I decided to use AI to turn the spreadsheet into one slide that covered the value, the phasing and the risk, in the language finance was looking for. Done by hand, it would have taken me until 1 a.m.
Because executives commit when they can see the whole plan on one page. The technology leader walked in with it, and the deal was signed the next day.
The result
The deal closed in September 2026, about twelve months after the pilot started, at an 8-figure total contract value and a seven-figure annual contract value over four years. It was the largest retail deal in my business that fiscal year, and it put me at 173% of quota year to date, #1 on my team. Commercial terms remain confidential.
The deal came down to one slide finance could defend.
How I’d run this play for AI buyers
Most AI buyers already have an incumbent and a team that doesn’t want to change. The obvious deal is a pilot that sits beside the old system. The bigger deal is the decision the customer is already circling. The same four milestones apply: treat the pilot as the start, widen the scope with the customer, build a case finance can defend, and make the final call easy to say yes to. And do the work the way the product works. I used AI to get the deal over the line, and that’s how I’d sell AI.
Adapted from my deal account and career records. Customer unnamed. Contract values are self-reported and shown as figure bands rather than exact amounts. These are contract values, not a claim of downstream customer ROI.