The short version
Because I had researched this Canadian regional bank deeply, and had been its customer since I was 9, I saw in the first meeting that its real problem was not the contact centre. Too few referrals from branches and commercial bankers were reaching its wealth advisors. I chose to sell the CEO a three-year plan to run every customer interaction in one system, not a fix for one department. That led to an 8-figure, bank-wide deal in January 2022, instead of a small contact-centre or referral-tool deal.
The obvious deal vs. the deal I built
- The obvious deal: replace a referral tool with poor adoption, or fix the contact centre. One department, one workflow.
- The deal I built: grow wealth-management assets by connecting every branch and banker to advisors. Every customer interaction, every business unit, one system, sold to the CEO as a 36-month roadmap.
The obvious deal was real, and it was easier. I shadowed the contact centre early, so I knew it well. But it would have left the bank’s biggest problem unsolved. I was also up against an incumbent CRM and ERP vendor and a home-built referral tool the bank had invested heavily in.
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 that most sellers skim their account list, and big accounts get dropped after one “no.” Most of my strategic deals came from accounts like that.
I decided to rank accounts by their ability, likelihood and interest to make an 8-figure investment, form my own view from industry data, investor reports and systems integrators, and then become the customer. I opened my first chequing account at this bank at age 9, with lawn-mowing money, and had a student line of credit there in university.
Because you can’t bring an executive a real point of view if all you’ve read is their website. My VP and I flew out to meet a new technology leader with a point of view on banking. In that first meeting, we found the real problem: referrals that never reached wealth advisors.
Milestone 2: Go wide, then deep
I saw that the bank had hired an independent evaluator with no experience on our platform. My access to the bank was limited during the assessment, but the evaluator’s findings would go straight to the C-suite.
I decided to invest in the evaluator: industry best practices, architecture and integration, and why one end-to-end platform beats separate tools for leads, referrals, customer records and marketing. We ran offsite design workshops of two to three hours around one table, went wide across the business first, then deep on architecture.
Because when you can’t reach the buyer, you teach the person who writes the buyer’s briefing. Going wide is also how the deal grew: from commercial referrals to retail customers in branches, and to growing the assets wealth advisors manage.
Milestone 3: Make the business case defendable
I saw that a deal this size had to go to the CEO, and that not every executive wanted to change platforms.
I decided never to pitch the purchase. I partnered with the executive who led customer experience and had a direct line to the CEO. With our enterprise architect, we built a 36-month roadmap tied to the bank’s own goals, with each business unit onboarded over 12 months. We wrote the proposal with our business-value team and refined it through several drafts with the bank’s own mobilizers.
Because a CEO doesn’t buy software. A CEO buys a plan they can defend to their board. The case was simple: give every employee the customer information they need, at their fingertips, for a better customer and employee experience.
Milestone 4: Executive commitment, and a team that can deliver
I saw that big deals die in the gaps: between teams, between executives and during pauses. This one slipped with org changes, then COVID paused it for about nine months.
I decided three things. First, use events to remove roadblocks, not to impress. At a regional banking summit in Chicago, the bank’s team met peer banks 12 to 24 months ahead of them. When buyers invest the time and cost to travel, they bring their real questions, and peers answer them. Second, keep executives connected when the deal is quiet: I worked with our leadership to set up 10+ meetings between the bank’s C-level and our Country Manager. Third, recruit the team before the customer asks for it: a small group of experienced leaders in architecture, business value and implementation, with architects in early and often.
Because the roadmap was about implementation, not procurement, there was always a real next step. When the bank was ready in late 2020, we restarted fast.
The result
The deal closed in January 2022, about two and a half years after the first meeting, at an 8-figure total contract value and a seven-figure annual contract value. The scope grew from one referral problem to a 36-month plan covering every customer interaction.
A CEO doesn’t buy software. A CEO buys a plan they can defend.
How I’d run this play for AI buyers
Today’s buyers are CEOs deciding who owns their customer conversations, their data and the AI agents that act on both. Most have never bought this before. The obvious deal is a support use case sold as a cost cut. The bigger deal is the growth problem behind it. The same four milestones apply: know the account better than anyone selling to it, see the whole business before designing anything, sell a plan the CEO can defend, and keep executives committed through every pause.
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.