Buying the Same Revenue Twice
“Find me another million” is four different assignments wearing the same sentence. Here’s where I’d look, and in what order.
If I walked into your $20M SaaS company tomorrow and you said “find me another million dollars,” I wouldn’t have an answer for you. I’d have questions. Smart ones, and probably some dumb ones too.
So you want a million in recurring revenue? Cash this year? Profit? Those are different assignments. And how much are you willing to change the business to get it? Some CEOs are happy to add services. Others would rather leave money alone than build a company they don’t want to run.
Once that’s on the table, I’d start in the same two places almost every time. Churn first, then expansion. Building a new source of demand can take longer than finding an opportunity among people who are already paying you.
They bought. They handed you a problem to solve. What I want to know is what happened next.
Start with the money that’s already leaving
You can have a strong acquisition engine and still be buying the same revenue over and over. New customers arrive, old ones go, everyone works harder than last year, and the number lands roughly where it started.
That’s an expensive way to stand still. A treadmill on steroids.
I spent four years building a first-party data activation platform, and churn was a significant use case. The thing that actually worked was refusing to trust any single signal. We read behavior against money: engagement on one axis, spending patterns on the other. The accounts worth worrying about were usually the ones that looked fine on one axis and had quietly slipped on the other. That gap is often where disengagement shows up first. Early enough to still do something about it.
The cancellation is the last event in a much longer story. A quiet account might be a happy account. It might also be a dead account that just hasn’t canceled yet. Logging in tells you somebody logged in.
Why does it take so long?
I talk to companies that tell me it takes six to twelve months before a customer starts genuinely using the tool.
I have a hard time with that one. You persuaded somebody to buy. They signed. And now they’re waiting the better part of a year to get anything out of the decision. I start wondering how long it takes a competitor to notice. If one does, you’re screwed.
Sometimes the reasons are real. But “enterprise software is complicated” is the kind of explanation that ends a conversation before anyone examines the actual work. In conversations like these, it hasn’t taken much pushing before somebody in the room recognizes that a thing measured in months could probably be measured in days. The question that got us there was embarrassingly simple: why does it take so long?
How much of that time is necessary work, and how much is a request sitting in somebody’s queue? Did a requirement from one difficult account quietly become mandatory for everybody? I’d look for the smallest useful outcome a customer can reach, then measure whether getting there sooner changes retention or expansion.
Expansion starts with what they do next
After churn, I’d find the customers getting real value and watch what they do immediately afterward.
Where do they export the data? What spreadsheet do they open? Who do they hire to finish the job? What keeps showing up in support long after somebody decided it was out of scope?
If people are already working inside your product, you have an unusually good vantage point on the problems sitting next to it. That’s a massive advantage most companies leave on the floor.
It doesn’t follow that every request deserves a feature. A large customer can make a persuasive case for turning your roadmap into their internal project plan. So I want to know whether several customers have the same problem, whether it costs them enough that they’d pay to make it go away, and whether you’re well placed to solve it.
The clues for that are usually spread across the company. Sales hears the thing a prospect would happily pay extra for. Customer success watches the workaround get invented two weeks after the contract is signed. Support answers the same question all week. Each interaction looks ordinary on its own. Follow one specific customer problem across all of those departments and you can see who has it, how often, and what it costs them.
Freed time isn’t a dollar of ARR
There may be money in the unglamorous work sitting around your revenue, too. How many people touch a renewal? Why does a routine account change need engineering?
I’d just be careful about what kind of money. Freeing up ten hours a week creates capacity. It becomes savings only if spending actually falls, and revenue only if you use that capacity to serve demand you couldn’t serve before. Retention works the same way: keeping revenue you were on track to lose isn’t growth above today’s run rate.
Being strict about this early saves everyone a lot of enthusiastic, magic-spreadsheet arithmetic later.
Make the million stand up to a few questions
Say, purely for illustration, you could retain $300,000 of ARR that was likely to walk, and sell a $10,000 annual add-on to seventy existing customers. Call that a million against the outcome you’d have had otherwise.
Now the real work starts. Which accounts make up that $300,000? Why do we believe they’re leaving? Where are those seventy customers? Has any of them said out loud that they’d pay $10,000?
If the opportunity evaporates the moment you ask for customer names, it was never ready to be in a forecast.
I’d go after the pieces where you can get evidence quickly. Examine one cohort. Change one onboarding path. Put a clear offer in front of a handful of the right customers. Decide up front what result justifies continuing, because deciding that afterward is how projects survive their own evidence. Then give one person responsibility for the commercial outcome across departments, or you can ship the feature, close the tickets and never once check whether the customer got enough value to stay.
So if you asked me to find another million, I’d start by getting much closer to the customers you already have. Where does value take too long to arrive? What do they still have to do for themselves after they’ve paid you?
Put that story together first. Then we can talk about where the next dollar comes from.
Know where this has to go, and not how?
Twenty minutes. Tell me where you want this company to be in two years and I’ll tell you what I’d go look at first.