whoismike.co Essay · 006
May 2026 7 min read Product · Monetization

The monetization mistake hiding in your roadmap.

A note on how this was written. I wrote this essay. I used AI as a thought partner — to push back on weak arguments, tighten prose, and ask me better questions than I'd ask myself. The opinions and the mistakes are mine.

There's a pattern I've seen in every product org I've been close to. Someone ships a feature. Someone else (usually finance) asks, "how does this make money?" And if the answer isn't immediate and direct — a new pricing tier, an upsell, a conversion gate — the feature starts to feel like a luxury. Something nice but not essential. The kind of thing that gets blocked in planning.

This instinct isn't wrong, exactly. It's just incomplete. And the gap between incomplete and wrong is where a lot of product strategy goes to die.

The monetization reflex

Most companies think about monetization as a direct relationship: build thing, charge for thing. And that model works — right up until it becomes the only lens you use. When every feature has to justify itself with a price tag, you stop building the things that make the product worth paying for in the first place.

I've watched this happen. A team debates whether to invest in a collaboration feature that won't generate revenue on its own. The feature loses. Six months later, churn ticks up and nobody can quite explain why. The explanation was sitting in the roadmap they rejected — a feature that would have made the product stickier, more embedded in people's workflows, harder to rip out. Not because it had a price. Because it had gravity.

The features that create gravity rarely show up in a revenue attribution model. They show up in retention curves, in expansion rates, in the speed at which a single user becomes a team. They are, in the language of spreadsheets, indirect. In the language of strategy, they're load-bearing.

What indirect monetization actually looks like

It helps to be specific. The features I'm talking about tend to fall into a few patterns:

Stickiness features

These make the product harder to leave — not through lock-in, but through accumulated value. Think of anything that gets better the more you use it: custom workflows refined over two years, integrations woven into how a team operates, historical data that would take months to rebuild. None of these need a price tag. They need to exist, because once they do, switching costs go up and retention follows. In an enterprise context, a deeply embedded workflow isn't just a feature — it's a competitive moat no competitor's pricing deck can match.

Shareability features

These are the ones that move the product sideways through an organization. A workflow one team builds that another team discovers. A report that gets forwarded to a VP who wasn't in the original deal. The recipient didn't buy anything. But they now have a stake in what happens at renewal — and in many cases, they become the champion for expanding the contract. This is how enterprise products grow without a sales motion for every seat.

Visibility features

These make the product's value legible to the people who sign the contract. Dashboards, activity logs, usage reports — the things that help a decision-maker see that the tool is actually working. In an enterprise platform, an admin dashboard isn't a nice-to-have. It's what gets a seven-figure renewal approved. Nobody upgrades because of a dashboard. But plenty of contracts get cut because nobody could point to one.

Why the math is hard

The reason companies underinvest in these features is that the math is genuinely hard. Direct monetization is easy to measure: you shipped a feature, you charged for it, revenue went up. Indirect monetization is a second-order effect. You shipped a feature, usage patterns changed, retention improved, expansion happened six months later. The causal chain is long and noisy, and most planning processes don't have the patience for it.

This is a measurement problem, not a value problem. The fact that something is hard to attribute doesn't mean it isn't working. It means your attribution model isn't capturing the full picture — which, if you've spent any time in analytics, you already knew.

There's also an organizational problem layered on top of the measurement one. Product teams think in features and engagement. Pricing and commercial teams think in tiers, deal structures, and ARR. When these groups don't share a language — or a planning process — indirect value gets lost in the handoff. The features that drive retention and expansion don't show up in a pricing model, so they don't get defended in the room where the model gets built. That gap is where a lot of quiet damage happens.

The companies that get this right tend to do two things. First, they track leading indicators — not just revenue, but engagement depth, cross-team adoption, time-to-value for new users. These are the early signals that indirect features are doing their job. Second, they give these features the same strategic weight as direct revenue features in planning. Not more. The same. Which is harder than it sounds, because when you're staring at a spreadsheet and one line says "$X in new ARR" and another says "improved retention cohort," the first one always feels more real.

A way to think about it

I keep coming back to a simple frame: every feature either earns money or earns the right to earn money. The features that earn money are important — that's how you have a business. But the features that earn the right are what make the business defensible. They're the reason someone stays long enough to upgrade, invites a colleague, renews without shopping around.

This shows up most clearly in packaging decisions. Whether a feature belongs in the base tier or behind an upgrade isn't just a revenue question — it's a strategy question. Put the wrong things behind a paywall and you starve the adoption that would have driven expansion. Leave the wrong things free and you leave money on the table. The craft is knowing which is which — and having the conviction to defend it when the spreadsheet pushes back.

If your roadmap is entirely the first kind, you're optimizing for this quarter. If it's entirely the second kind, you don't have a business. The ratio is the strategy.

The real risk

The real risk isn't building too many indirect features. It's building none — and then wondering why your product feels transactional, why users churn at renewal, why growth is a treadmill instead of a flywheel.

The companies I admire most are the ones where someone, at some point, had the nerve to ship a feature that didn't make money and couldn't easily prove it would. They shipped it because it made the product better in a way that was hard to quantify and easy to feel. And then, quietly, it became the reason everything else worked.

That's the thing about indirect monetization. It never takes credit. But take it away and the whole system notices.