Square's public roadmap serves a dual purpose. While it informs customers, its primary internal function is to create accountability. Committing to features publicly forces the organization to deliver on its promises with speed and quality, preventing internal delays.
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The CRO, not product marketing, is closest to the customer and knows what they will buy. The product roadmap should be a collaborative effort driven by the CRO, who can directly tie feature delivery to ICP expansion and revenue forecasts. This creates accountability and predictable growth.
CEO Dylan Field combats organizational slowness by interrogating project timelines. He seeks to understand the underlying assumptions and separate actual work from "well-intentionally added" padding. This forces teams to reason from first principles and justify the true time required, preventing unnecessary delays.
A product roadmap's value is in the planning process and aligning the team on a vision, not in rigidly adhering to a delivery schedule. The co-founder of Artist argues that becoming a feature factory focused on checking boxes off a roadmap is a dangerous trap that distracts from solving real customer problems.
Square's product development is guided by the principle that "a seller should never outgrow Square." This forces them to build a platform that serves businesses from their first sale at a farmer's market all the way to operating in a large stadium, continuously adding capabilities to manage growing complexity.
Gumroad's CEO credits their rapid development to his role as a solo decision-maker. This structure eliminates the lengthy processes of gaining internal buy-in and creating extensive documentation (PRDs, specs) common in larger organizations, which are often more about alignment than execution.
A dual-track launch strategy is most effective. Ship small, useful improvements on a weekly cadence to demonstrate momentum and reliability. For major, innovative features that represent a step-change, consolidate them into a single, high-impact 'noisy' launch to capture maximum attention.
When a product team is busy but their impact is minimal or hard to quantify, the root cause is often not poor execution but a lack of clarity in the overarching company strategy. Fixing the high-level strategy provides the focus necessary for product work to create meaningful value.
Go beyond visual roadmaps. Create a monthly written document for executives that explains *why* the roadmap changed, details priorities, and includes data from recent launches. This forces intentionality, builds trust, and fosters deeper, more accountable conversations with leadership.
Robinhood is shifting its planning process to focus on what will be announced at its next public product keynote. Instead of setting abstract internal goals, this aligns the entire company around concrete, customer-facing deliverables and creates a powerful, immovable deadline for shipping.
A single roadmap shouldn't just be customer-facing features. It should be treated as a balanced portfolio of engineering health, new customer value, and maintenance. The ideal mix of these investments changes depending on the product's life cycle, from 99% features at launch to a more balanced approach for mature products.
