The Monetization Gap.

If you're on the vendor side, it's money left on the table. Underpricing. Revenue leakage. Value you created but didn't capture.

If you're the customer, the problem is the opposite: surprise fees. Forced bundles. The chasm between what you're paying and what you're actually getting.

What you see depends on which side of the table you sit on.

Here's what I've learned after two decades and hundreds of executive conversations: You're both right. And you're both losing.

At first glance, this looks like a pricing issue. It's not.

I know this because I've seen this movie before.

Back when SaaS was first emerging—before it was even called "SaaS"—I was an industry analyst trying to measure its impact. And I had a problem.

If I counted these new software companies the same way I counted legacy vendors, I'd be comparing apples to oranges. Legacy vendors recognized perpetual license revenue upfront. The new cloud companies recognized revenue over time. Measuring them the same way would dramatically understate the size and impact of what was happening.

So I created an entirely new forecast. A new way of measuring software.

Because you can't measure a new paradigm with an old scorecard.

We're at that moment again. 

Everyone's focused on pricing models, retention tactics, and bundling strategies. They're solving the wrong problem. 

The real issue isn't how you're pricing. It's how you're measuring. We're still using the same scorecard we used for the old model. Measurement problems create incentive problems. Incentive problems create trust problems.

Let me show you what I mean.

Last month, at a dinner for cross-industry finance leaders, we talked about the usual suspects. AI. Return-to-office mandates and the impact on pets. The macro outlook, tariffs, and crypto.

Then someone said, "Our (CRM) SaaS renewal came in at 6x,” and no one was shocked. People around the table nodded in resigned recognition. Same same. 

Everyone's being told we're at the beginning of an exciting new era. But finance leaders already feel like they're out of runway, and they are definitely out of patience.

The data confirms what they're feeling:

Innovation no longer creates excitement. It triggers anxiety.

AI features. Usage tiers. Complex bundles. SaaS-era companies announce these with excitement.

And to be clear, their customers are counting on their major platform vendors to deliver AI capabilities ASAP. They've already invested in these systems—sunk costs, compliance, risk management. They tell me they'd rather get modern tech from vendors they know than buy multiple point solutions from vendors they don't.

But the capabilities are taking too long to materialize from out of the marketecture. And when they do arrive, finance hears something else: unpredictable cost. Not just the price on the invoice, but the operational burden, the testing and change management, the budgeting nightmare.

Too slow to deliver. Too expensive when they do. That's the gap.

SaaS was supposed to fix this. Instead, history is repeating itself. We're at the beginning of a new platform shift, and finance leaders already know how this story ends. Pricing tactics have replaced new customer acquisition as the primary growth lever. It's the exact extortionary playbook that killed the late '90s software era and birthed SaaS in the first place.

When the pricing conversation starts, the spreadsheet takes over. Customer-obsession is pushed aside for the moment. The question shifts from "What's the best way to create value?" to "What's the maximum we can extract?"

That shift—that moment—is the Monetization Gap in action.

And here's what makes it so dangerous: both sides lose, but neither sees it coming.

Right now, vendors are bundling AI capabilities into across-the-board price increases. Charging customers whether they adopt the features or not. Justifying 50%, 100%, and sometimes 600% increases by pointing to "innovation" that customers haven't touched.

This violates a core tenet of SaaS: monetize the value delivered, not the value promised.

When you charge for capabilities customers don't use, you're not creating value. You're extracting value while eroding trust. And that erosion? It's accelerating.

For customers, it feels like confusion by design: pricing pages that obscure more than they reveal, renewal increases that blindside finance teams, bundles that force payment for features they'll never use, and constant anxiety about what the bill will look like next quarter.

For vendors, the damage shows up differently but just as painfully: customers churning silently without warning, sales cycles dragging on as procurement teams scrutinize every line item, discounts deployed as blunt instruments just to close deals, and growth that stalls at a ceiling nobody predicted.

When customers can't forecast their software spend, they can't plan their business. And that uncertainty accelerates the outcome vendors fear most: rigorous evaluation and aggressive replacement.

The Monetization Gap creates an environment where dark patterns thrive. 

Dark patterns are manipulative design elements that trick users into decisions they wouldn't otherwise make. Confusing interfaces. Hidden cancellation buttons. Forced bundles disguised as defaults.

The poster child? Amazon's "Iliad Flow."

In June 2023, the FTC sued Amazon for knowingly tricking millions of customers into signing up for Prime subscriptions and then making cancellation nearly impossible. The cancellation process—which Amazon internally named "Iliad Flow" after Homer's 16,000-line epic poem—required:

Meanwhile, signing up for Prime? One or two clicks.

Internal documents revealed that in 2017, the Iliad Flow led to a 14% drop in cancellations, as fewer members reached the final page. Amazon didn't accidentally make it hard to cancel. They engineered difficulty and measured its effectiveness.

The FTC's complaint was damning: "The primary purpose of its Prime cancellation process was not to enable subscribers to cancel, but to stop them."

In September 2025, Amazon settled for $2.5 billion—$1.5 billion in consumer refunds plus a $1 billion penalty.

We treat pricing and packaging as operational decisions.

They're actually trust signals. When companies lose trust in their value proposition, they compensate with friction. When you can't keep customers through value, you trap them through design.

In B2B SaaS, dark patterns show up as pricing pages that hide actual costs behind a "Contact Sales" button, cancellation flows requiring multiple retention conversations, downgrade options buried six levels deep, surprise renewal increases, and extraneous features you can't opt out.

Every one of these says the same thing the Iliad Flow did: "We don't trust our value to keep you here."