Insights on fintech, banking & partnerships

You've done the discovery call. The banker was engaged, asked real questions, said things like "we could really see this fitting into what we're trying to do here." You walked away thinking the deal was warm.

Then nothing. A follow-up email. A polite response. A slow fade.

If that pattern is familiar, I want to offer you a diagnosis that has nothing to do with your pitch, your demo, or your pricing.

The problem is categorization. And until you solve it, every meeting you take will produce the same result.

I spent 23 years inside Jack Henry, and the last six working alongside FinTech founders trying to sell into community banks and credit unions. In that time, I've watched brilliant products stall at the exact same point — not because they weren't good enough, but because the banker couldn't sort them. No shelf, no deal. It doesn't matter how impressive the technology is.

This post is about what that problem actually is, why it persists even among sophisticated founders, and the five-part framework I use with clients to solve it.

Table of Contents

• What the Category Conundrum Actually Is

• The Case Study: 40 Discovery Calls, Zero Conversions

• Why Anchoring Is the Answer

• The Five Anchors Framework

  • Anchor 1: The Pain Anchor

  • Anchor 2: The Task Anchor

  • Anchor 3: The Technology Anchor

  • Anchor 4: The Process Anchor

  • Anchor 5: The Emotion Anchor

• The Core Rule: Anchor to the Present, Not the Future

• Three Practical Steps Before Your Next Bank Meeting

• Key Takeaways

• FAQ

• Related Reading

What the Category Conundrum Actually Is

Bankers don't evaluate vendors from scratch. They sort them.

The moment a FinTech walks into a meeting — or clicks into a video call — the banker's brain is already working through a checklist, consciously or not. Where does this go? What budget line does it come from? Who internally owns this category? What does vendor management need to do with it? What examiner category does it fall under?

This is not a flaw in the way bankers think. It is an entirely rational response to the volume of vendor outreach they receive and the complexity of the institutions they manage. They are running organizations with fiduciary obligations, examiners, boards, and communities depending on them. Mental categorization is a survival skill.

The problem for FinTech leaders is that the most innovative products — the ones that should theoretically win — are also the hardest to sort. They don't fit neatly into core IT. They're not a loan product or a payments product or a compliance tool or a CRM. They're genuinely new. Which is also why they stall.

When a banker can't sort you, they don't reject you. Bankers are almost universally polite. They smile, engage, ask thoughtful questions, and tell you they'll follow up. What they're actually doing is parking you. The deal sits in a mental holding queue that never converts to action because there is no internal pathway for it. No budget owner to bring it to. No vendor management process to initiate. No champion who knows what to call it.

Being interesting to a banker is not the same as being understood by one and interesting does not get you to a contract.

The Case Study: 40 Discovery Calls, Zero Conversions

A founder I worked with had done everything right. He had a genuinely strong product. He had done the outreach, booked the meetings, and conducted approximately 40 discovery calls with community banks and credit unions. By every external measure, those calls went well. Bankers liked him. They asked real questions. They said things like "this is really interesting" and "we could see this fitting into what we're doing."

Zero conversions. No next steps. No timelines established. No deals in motion.

He came to me convinced the problem was his demo. He wanted to tighten his messaging, add a case study, adjust the ROI slide. He had done the rational thing a founder does when they're not closing — look at the pitch and try to improve it.

My diagnosis was different. His product didn't fit neatly into any existing category at the banks he was pitching. It wasn't core IT. It wasn't a lending product. It wasn't compliance software. It wasn't a CRM. It was genuinely innovative — sitting at the intersection of two or three categories without owning any of them completely.

That was the problem. Not the demo. Not the messaging. Not the ROI slide.

The bankers he spoke with couldn't answer the internal questions that would move a deal forward: What budget does this come from? Who owns it? What do I call it when I bring it to my vendor management committee? Without answers to those questions, the most natural path is to do nothing. And that's exactly what they did.

The sale doesn't happen at the demo. It happens when the banker finally understands what you are. If that moment never comes, no demo will save you.

Why Anchoring Is the Answer

In 2001, Apple launched the iPod. The device contained a one-and-a-half inch micro hard drive capable of storing and playing back compressed audio files at variable bit rates through a proprietary digital interface. None of that was in the launch copy.

What Apple said was: "A thousand songs in your pocket."

Four words. No specs. No architecture diagram. No feature breakdown. Just a shelf built around a frustration people already had — the CD binder, the cassette case, the limited soundtrack you could carry through an airport.

Nobody needed to understand how the iPod worked. They just needed to feel the relief of not carrying that binder anymore. The anchor did the work before the product had to.

The same mechanism applies in every bank meeting you walk into.

Before you explain a single feature, you have one job: give the banker a shelf to put your product on. Root your solution in something they already understand, already feel, or already live with every day. Not because bankers are unsophisticated — they're not. Because every buyer, in every industry, needs a mental category to take the next step. When they can't categorize you, they park you.

Most FinTech founders believe their job in a bank meeting is to explain what they built. It isn't. Their job is to do the translation work the banker shouldn't have to do.

Anchoring is not dumbing it down. It is earning the pitch.

You polish the deck. You nail the demo. The banker across the table is nodding, engaged, saying things like "this is exactly what we need." You leave the meeting confident.

Then nothing happens.

You follow up. They say they're "still evaluating." You follow up again. They say "let's circle back after Q1." You refine the pitch, book more meetings, and the exact same thing happens — new bank, same outcome.

Most founders run the standard diagnostic at this point: unclear pitch, wrong ICP, bad timing. So they rewrite the deck. They narrow the target. They wait for a better quarter. And the pattern repeats.

Here's what I want to tell you, because I've watched this loop play out across dozens of FinTech founders: you're solving the wrong problem. The issue is not your pitch. It's not your timing. It's not your ICP.

It's a placement problem. And until you diagnose it correctly, you'll keep optimizing inputs in a broken system.

Watch me explain it in this video.

For the complete framework, read the full guide.

What the Category Conundrum Actually Is

I call this the Category Conundrum.

It happens when a genuinely novel FinTech product enters a market that is institutionally built around categories that don't include it. Banks and credit unions are not free-form buyers making intuitive decisions. They operate through a structured internal sequence before any purchase can move forward.

When your product doesn't map to a category they already recognize, that sequence breaks. Not slows. Breaks. And the result isn't a "no" — it's an indefinite suspension of forward movement that looks, from the outside, exactly like a timing issue or a pitch problem.

This distinction matters enormously. A pitch problem responds to iteration. A placement problem doesn't. If you're iterating on a placement problem, you're doing precision work in the wrong direction.

The Institutional Buying Machinery

To understand why this happens, you need a clear picture of how institutional buying actually works. I model it as three sequential steps, and every step has to complete before the next one starts.

When a banker encounters your "next-gen orchestration layer" or your solution "redefining real-time decisioning," they don't reach out for clarification. They attempt a rapid internal translation: Is this fraud? Is this data? Is this core banking adjacent? When no answer surfaces in the first few seconds, they don't flag confusion. They nod. They engage. They say "that's interesting." And the meeting ends warmly for both parties.

You leave thinking it went well. The banker leaves not knowing what you do.

This is the Category Conundrum in action — and it's invisible while it's happening because the feedback signals look positive.

If your a Fintech Founder with an innovative or new solution for banks, your deck probably isn't the problem. I've spent years working with FinTech founders who are selling genuinely innovative products into banks and credit unions and I keep watching the same thing happen. The meetings go well. The bankers are nodding. Everyone agrees it's a good idea. And then nothing happens…

Founders blame the pitch. They rewrite the deck. They qualify the ICP more carefully. They wait for Q1. And the same pattern repeats; meeting after meeting, quarter after quarter, deal after deal that never closes.

Here's what I've come to understand: the problem isn't the pitch, it's a placement failure. When your product doesn't fit an existing institutional category, banks and credit unions cannot move forward with it because their internal buying machinery requires a category to function.

Without one, the machinery stops.

I call this The Category Conundrum.

This post lays out the full framework: what the Category Conundrum is, the three signals that tell you you're in it, and the three remedies that get you out. Every other piece in this content cluster links back here because this is the root diagnosis everything else builds on.