Which Roadmap Path Are You On?

Running a business would be so much easier without customers. At least without them bugging you all the time.

If you have built software for larger companies, you know what I mean. The requests never stop. They want to know what is coming next quarter, next year, even two years out. They need slides for their leadership teams, budgets to defend, resources to plan. Meanwhile, you are trying to build something valuable without painting yourself into a corner.

Most advice on how to handle this tension assumes you have a choice in the matter, but that’s not always the case. As sad as it is, your roadmap approach is not a philosophy you get to conjure up yourself. It is a reflection of your market structure.

There are three different paths here, each with its own rules, advantages, and traps. The mistake is not being in any particular one. The mistake is not knowing which path you are on.

Path One: Many Small Customers

You have thousands of customers, maybe tens of thousands. No single one represents more than a fraction of your revenue. If any individual customer leaves, you’ll hardly notice.

This is the approach that 37Signals has, and why their writing feels so enticing. They can famously ignore long-term roadmaps because they have preserved the structural freedom to do so. Six-week cycles, total focus, building what matters right now without the weight of promises made six months ago.

The advantage here is freedom. No single customer can derail you, so you can build what you believe in, change direction when you learn something new, and ignore requests that do not fit your vision. Your GTM is likely product-led. Customers sign up, swipe a card, start using. No procurement meetings asking for roadmap commitments before they buy. More importantly though, it is founder-led. The business is a reflection of how the founder wants to run their business.

That’s why the trap is arrogance. You can ignore customers, so you stop listening entirely. You lose touch with the market because you never had to care. The feedback loop is usage data, not conversation, and it is easy to mistake silence for satisfaction.

Discovery here is a luxury you might not use. You have the freedom to experiment, ship fast, learn from usage, and pivot without asking permission. Continuous discovery in its purest form. But the arrogance trap means many companies on this path skip it entirely. They build what the founder wants, assume it is what customers need, and never close the loop. Freedom without curiosity is just guessing with confidence.

Most companies cannot walk this path, and that is fine. It is a structural position that depends on choices made early: staying bootstrapped or taking funding that does not require rocket shit growth, building for a sustainable future, not an outsized one, keeping the product simple enough that it sells itself. If you took investor money that expects 10x growth, or if you landed a few large customers early and built around them, this door has already closed. That is not a failure. It is just a different path.

Path Two: Mixed Portfolio

You have a diverse customer base. Some big customers, many small ones. No single account dominates, but the large ones matter enough that you cannot ignore them entirely.

The advantage here is optionality. Big enough customers to for a potential massive revenue, broad enough base that you can say no when you need to. You have leverage to choose which game to play on any given deal.

This is where a rolling confidence roadmap actually works. The approach Varun Paramar described for Miro: 80% certainty for the next quarter, 50% for the quarter after, themes and vision beyond that. You are honest about what is a commitment and what is a bet. Customers get enough to plan with, you keep enough flexibility to adapt.

Your GTM is probably hybrid. Some product-led, some sales-assisted. Enterprise customers who need conversations, but also a base of smaller customers who just show up.

There are two potential pitfalls here.

The first is drift. You start listening disproportionately to the big logos. You build what they ask for. You bend the roadmap to keep them happy. Slowly, without noticing, you let a few accounts accumulate leverage they should not have. You have drifted into Path Three dynamics while still thinking you are on the second path. If you are in a mixed market but feel trapped by a handful of demanding customers, the problem might not be your roadmap process. It might be your sales strategy or your product-market fit.

The second trap is false uncertainty. You say you operate with honest confidence levels, but you never actually drop anything. You always deliver. Customers learn to ignore the percentages because they know you will come through anyway. Then when you finally do drop something, they are blindsided. The honest uncertainty was never real. It was theatre.

Discovery on this path is easily available, but requires discipline. You can talk to customers, run experiments, validate before you commit. Continuous discovery works well because you have such a range to talk to. The danger is that discovery gets captured by the loudest voices. Your biggest customers have opinions, and those opinions are not always representative. True discovery means seeking signal beyond whoever is emailing your sales team this week.

Path Three: Few Large Customers

Your market has a handful of buyers. Telcos, utilities, big enterprise, specialized verticals where there are only a few hundred possible customers in the world. Each deal is significant. Losing one or two would be a serious problem.

This is not a failure state. It is a legitimate market structure with real advantages. You have depth. Real relationships with customers who depend on you operationally. Meaningful revenue from each account. Mutual dependence, because they cannot leave easily either. You are building something that actually matters to their business, not a tool they could replace next quarter.

Your GTM is sales-led with long sales cycles. Every deal involves humans talking to humans. Procurement, legal, implementation timelines. The roadmap is part of the sales process because they are not just buying what you have today. They are buying a well-defined future.

The approach here is manufactured certainty. Customers on this path will not process uncertainty fairly. Tell them something is 50% likely and they will either round it up to “yes” when they want the feature or round it down to “no” when evaluating you against a competitor making firmer promises. Or they will ignore the percentage entirely and just remember that you said you would do it.

So you do not give them uncertainty to process. You show them what is already in motion. Hidden roadmaps, where you are actually three months into the work before you present a six-month plan. You promise what you are confident you can deliver and stay vague on everything else.

The trap is overpromising. The strategy is sound, but estimation is hard. You cannot show uncertainty, but you also cannot actually eliminate it. Eventually you will miss a deadline, and you will not have “we said it was only 50%” to fall back on. You just look like you could not deliver.

The more customers you have, the more difficult it becomes. Something vital comes up, and you need to switch focus. The three month buffer you created can vanish quite quickly if you’re not hyper-focused on the roadmap you defined. It works until the estimation fails. That doesn’t mean approach is wrong. The execution is just hard. And when you miss here, you miss without excuses.

Discovery on Path Three is the hardest. You often cannot talk to end users directly. Your customer is not your user. You are selling to enterprises who deploy your product to people you will never meet. So you get creative. Treat pilots as research opportunities, not just sales milestones. Instrument your product to tell you what users cannot. Turn customer support into a discovery channel. Build relationships with champions inside your customers who can translate what their users actually need. Discovery does not stop because access is limited. It just gets harder.

Know Your Path

Each Path has something the others lack. Freedom, optionality, depth. The mistake is not being in any particular one. The mistake is playing by rules that you follow on a different path.

Your roadmap process is downstream of your market structure, your GTM, and your financing. Understand the constraints they create, and the roadmap question mostly answers itself.