Essay · Tom Dillard · October 19, 2026 · 5 min read
Two to Ten: Expansion Is Designed, Not Discovered
Growing the largest accounts is an operating model. It is not a relationship story, and it does not happen because everyone agrees it is important.
I grew the base of accounts spending more than a million dollars a year from two customers to ten, and we reached the corporate target mid-year.
People hear that and assume it is a relationship story. Great people, strong rapport, trusted advisor, and so on. Relationships were necessary. They were nowhere near sufficient. What produced it was an operating model, and the model is reproducible.
Start with the uncomfortable part. Expansion is the highest-margin revenue available to a company, and it is almost always the worst-managed. New logo gets a process, a stage model, a forecast, a comp accelerator, and executive attention every week. Expansion gets a hope, an annual account plan nobody reads, and a customer success manager with sixty accounts and no commercial mandate.
Then everyone is surprised that expansion underperforms.
Four decisions made the difference for us.
First, tiering that is honest. Not every account can carry a million dollars, and pretending otherwise spreads effort evenly across a portfolio where the opportunity is wildly uneven. We tiered by realistic ceiling rather than by current spend. Some of our largest current accounts were near their ceiling and got maintained. Some mid-size accounts had ten times their current spend available and got the investment. That reallocation is where the growth came from, and it requires saying out loud that some accounts will get less attention, which most organizations cannot bring themselves to do.
Second, a plan per account with named sponsors on both sides. Not a template filled in for a quarterly review. A short document that answers: what does this customer need to accomplish in the next eighteen months, which parts of that can we serve, who inside their organization owns each one, who on our side owns the relationship with that person, and what is the sequence.
Third, and this is the mechanical change that mattered most, we reviewed the plans rather than the pipeline. Once a month, top accounts, and the meeting was about the account strategy, not about what was going to close this quarter. Pipeline reviews pull attention to the next ninety days by design. Expansion is a two-year motion. If your only recurring forum is the forecast call, you will systematically starve every initiative whose payoff sits beyond the quarter, and you will do it while sincerely believing expansion is a priority.
Fourth, coverage that matched the ambition, and this is where the people side becomes a commercial variable rather than an HR one. A million-dollar relationship inside a large enterprise is not one relationship. It is eight or ten, across functions that do not necessarily talk to each other. If one seller owns all of it, the account grows to the limit of that one person’s calendar and stops.
“You cannot run a land-and-expand motion on a team with high turnover. The motion is longer than the average tenure.”
So we staffed the accounts that could carry weight, and we accepted that this meant fewer accounts per person. And then we kept those people, because the entire model depends on continuity. An expansion plan is an eighteen-month bet on relationships that a specific human being is building. Churn that human being at month nine and you have not lost a seat, you have lost the bet.
That is why the retention question and the expansion question are the same question. You cannot run a land-and-expand motion on a team with high turnover. The math does not work, because the motion is longer than the average tenure.
There is a strategic argument underneath all of it worth making to a board. Expansion revenue is cheaper to acquire, closes faster, retains better, and is more predictable than new logo. It should therefore be the most disciplined motion in the company. In most companies it is the least disciplined, purely because it grew up as an afterthought and nobody ever went back and designed it.
One caution. Expansion is not upselling. Upselling is selling more of what you already sold, and there is a ceiling on it that arrives faster than anyone expects. Expansion is finding the next business problem in an organization that already trusts you, which requires curiosity about their business rather than fluency in your product. Those are genuinely different skills, and the second one is rarer and harder to hire for.
If you want to know whether your expansion motion is designed or accidental, ask one question at your next leadership meeting. Name the three accounts that will grow the most next year, and tell me the mechanism by which each will grow.
If the answer is a list of accounts that are simply large today, you do not have a model yet. You have a hope with a customer list attached.
Tom Dillard is Chief Revenue Officer of RightStar Consulting Partners, LLC and Principal of The Vanguard, the house where leadership architecture meets enterprise revenue operations. He spent three decades building and scaling enterprise software revenue organizations, twice ranked the number one revenue producer worldwide, and now advises boards and chief executives on revenue strategy, revenue operations, and go-to-market design. The Vanguard publishes every Monday.