Contributors · 2
- Kyle Barnholt
- Alice Humble
Q&A2026-08-10
Building a cloud software roadmap requires balancing the demands of large enterprise clients against a coherent product vision. This article explores practical strategies for managing these competing priorities, drawing on insights from product leaders who have successfully scaled cloud platforms. Learn how to enforce replacement tradeoffs and favor reusable patterns over custom solutions when planning your product's future.
Contributors · 2
Kyle Barnholt<CEO & Co-founder, Trewup>The rule that helped us most was the replacement rule. When we accepted an urgent request, we had to identify what work it replaced and explain why the change helped the business. This created better focus because teams started thinking about tradeoffs before adding new work. It also changed how we viewed the roadmap and encouraged more careful decisions.
We paired this rule with a regular review of the work we delivered against our main goals. If a new idea did not support those goals, we asked for a stronger reason to move ahead. This helped us stay flexible without becoming reactive. We found that customers valued our focus when we explained choices clearly.
Alice Humble<Co-Founder & CEO, Shortlists>My filter is whether the request points at a problem lots of customers have, or just this one deal. Sales naturally argues for whatever unblocks the deal in front of them, and sometimes that request is a gift because it's a real gap we'd been ignoring. But if building it only makes sense for one logo, that's a warning sign, not a roadmap item. I try to separate "this customer wants X" from "this customer has a problem X happens to solve," because the second one usually generalises and the first one just gets you a pile of bespoke features nobody else touches.
The thing that keeps us honest is a standing rule that we don't commit to anything roadmap-level in the room where the deal's being discussed. Sales can always say "I'll find out," never "yes." Then it goes to a short weekly pass where we look at what's being asked for across all the deals together, and a pattern that shows up three times jumps the queue while a one-off waits. Deciding away from the heat of a specific deal is what stops the loudest customer from quietly becoming our product manager.
Turning enterprise custom work into premium add ons aligns revenue with effort. Package the most common asks into modules controlled by plan and price. Base price on clear value signals like seats, usage, or required compliance.
Share a simple menu so sales can shape deals without risky promises. Track how often customers buy the add on, the effect on churn, and profit to improve offers fast. Draft a pricing test and set up a pilot with two design partners next quarter.
An enterprise lane with clear SLAs protects trust without derailing the roadmap. Define intake rules, severity levels, and response times that match contract terms. Staff a rotating crew that can resolve issues while the core team stays focused.
Share status and after action reports so customers see steady, clear progress. Feed root causes into maintenance work to shrink future noise. Write the SLA policy and launch the lane with a small pilot this month.
An extensible architecture keeps enterprise needs from bending the core product. Define clean seams where custom logic can live without forking code. Use stable APIs, events, and toggles so heavy demands land at the edges.
Guard the shared data model and workflows with clear contracts and tests. This reduces upgrade pain, speeds onboarding, and keeps shared cloud health strong. Draft an extension blueprint and agree on the first two seams this month.
A clear split of roadmap capacity protects product vision while serving enterprise deals. Set fixed percentages for innovation, enterprise asks, and maintenance based on strategy and cost of delay. Review the split on a steady cadence so leadership can trade scope, not time.
Tie each bucket to simple KPIs, such as adoption rate, revenue won, and defect burn down. Publish the split and current spend so sales and customers see fair trade offs. Set and publish this split today.
Dual track discovery reduces risk while keeping delivery moving. One stream explores real problems with customers and proves value early. The other builds proven slices with tight feedback from early users.
Use light tests like mockups and manual trials to learn cheaply. Sync both streams on a weekly beat so new insights adjust the plan fast. Book a standing discovery session with key accounts and start this rhythm now.