Hey, it's Jose.
Years ago at Mastercard, we were looking to launch a new loyalty solution for a new type of business. Not an issuer, not a traditional merchant relationship. Merchant and deal-loyalty providers.
We had the technology. Payment rails can verify a transaction in real time, tie it to an account, settle it cleanly. Loyalty and deal providers were doing something close to that already, just not very efficiently. It felt like an easy fit.
Before we built anything, I started with a listening tour to really understand the challenges of all the players involved. This was the daily-deals heyday, and merchants running deals were doing real volume. I found out that the process was manual and prone to error. Merchants had to verify a deal redemption by hand (on a piece of paper!), reconcile, hope they marked everything correctly.
That was the big problem, and once we knew it, putting together the technical solution was not that difficult. The ability to eliminate manual reconciliation became the positioning, because it came from them, in their words, describing their pain.
In my experience, it always pays off to confirm someone is in enough pain that they'd pay for the fix you're offering. There are a lot of solutions that "could be useful." Only a few are useful enough that someone will hand you money for them.
The tell
I keep seeing the same move at mid-market companies. The core business is doing fine. Win rates are reasonable, retention is acceptable, and the board asks the natural question: where do we grow next? The answer is almost always a new vertical. The product works, the team knows how to sell it, so why not plant it somewhere new?
There's a diagnostic I run in almost every GTM conversation now. Ask a few of your best customers, unprompted, why they bought.
The answers split into two kinds. The first sounds like: "We had a specific problem, looked at three options, and yours was the only one that actually fixed it." The second sounds like: "We were evaluating a few tools and yours came out ahead."
Both close deals. Only one tells you who you're actually built for.
The first is describing a problem they were already trying to solve, the same way those merchants were describing broken deal verification before I ever pitched them anything. When buyers are already trying to solve the problem, they find you, they push their own procurement, they become champions before you've asked. The second is describing a benefit they discovered after the sale. You end up fighting for budget against things they actually care about.
The right to win
This is where vertical expansion gets expensive.
Every market has incumbents. Every buyer has a status quo. Your right to win in a segment isn't whether your product can technically serve that buyer. It's whether the way you deliver value is actually better than what they already have.
I don't have a formal scorecard for this yet. But I keep coming back to the same question: would a prospect in that segment recognize your reference customers, or are you learning their workflow for the first time in the sales cycle?
If the answer is "not yet," you don't have a right to win. That's not a reason to walk away from the vertical. It's a reason to treat it as an investment, not a quick win with a few tweaks to the deck.
The expensive mistake isn't a bad product. It's confidently putting quota and pipeline coverage behind a segment where you have no real advantage, while the segment that already wants what you sell gets less attention than it deserves.
What good looks like
Companies that do this well share one habit. They can say, in a single sentence, the specific problem they solve for a specific kind of buyer. Not a category. A problem.
Not "we help revenue teams improve efficiency." More like: "We help sales leaders at companies with 30 to 80 reps figure out why their pipeline is stalling before it shows up in the forecast." That names who feels the pain, what it is, and when it matters.
Get that sentence right and everything downstream gets easier. Your reps know who to call. Your team knows what they're actually diagnosing. And when you do move into a new segment, you have a real test: does it feel this problem the way your core segment does?
We didn't write the loyalty positioning at Mastercard until the merchants gave it back to us in their own words. That's still the test I trust most.
If you asked your three best customers to describe the problem you solve, no coaching, would the answer match your pitch deck?
Jose Celorio Founder, GTM Reloaded
Former Strategist at Google, Mastercard & Deloitte Consulting
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