When Payment Tech Pitches Fail (And Why Mark Mihill's Booked)
- Cormac Repman
- 2 days ago
- 2 min read
We watched a pattern emerge across six cold calls pitching payment processing solutions. Four rejections came back the same way: efficient ACH, satisfied with their current cards, no friction to solve. Meanwhile, a rep booked a meeting with a prospect using an entirely different payment method. The difference wasn't sophistication or company size. It was acute pain within the existing category.
ClickUp's Head of Finance Operations rejected the pitch clearly. They already have efficient ACH and credit card processes in place. No friction. No deal. Similar responses from other companies with mature payment infrastructure. Their systems work. They've optimized for the category they're in. From their perspective, there's nothing to fix.
But here's where it breaks. One prospect booked despite using cards as their primary payment method. His company was 95 percent credit card dependent. Not because cards were good. Because cards created a specific, measurable cost problem. Every transaction stung. Every margin compressed. Cards were the existing category, and within that category, the friction was acute enough to overcome inertia.
We're seeing this across other verticals too. Cenovus Energy booked a meeting not because their current operations process was broken, but because they identified a gap. They manage plant operations with paper plans in the field. They're rolling out mobile devices. The tools exist. The gap exists. That gap got them on a call.
The laundry business booked because they're evaluating their entire marketing stack. Not because their current platform failed, but because they're in active comparison mode and paying attention to alternatives. Different driver, same lesson.
What doesn't work: assuming satisfaction equals stickiness. A company with an efficient payment process isn't stuck. They're comfortable. Comfort is stable until friction appears.
What works: finding acute friction within the existing category, not between categories. Your prospect might be happy with their ACH process and their card process. They're not happy about the 200 basis points they're eating on consumer transactions. Or the reconciliation overhead. Or the integration gaps. The category didn't change. The pain within it did.
This means your targeting needs precision. Don't pitch payment solutions to companies with no current friction. Pitch to companies where the existing solution creates measurable cost or operational drag. Look for the margin compression, the manual reconciliation work, the lost transactions, the vendor limits. Those are within-category problems that overcome satisfaction.
We also notice that stage matters. A company in active growth or migration (rolling out new devices, launching new business units, trialing new platforms) develops new friction. Their old solutions worked fine at scale N. At scale N plus one, they don't. That's not about better technology. That's about outgrowing fit.
The pattern holds: satisfaction is stable until friction appears. When friction appears within the existing category, even a satisfied customer will listen. The pitch isn't about replacing their stack. It's about solving the specific, measurable problem that stack created.
Target the pain, not the category.
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