Agile Estimation Platform Redesign for PlanningPoker.com
Development Team Coordinator·352 Inc. and Mountain Goat Software·2015
Enterprise0-to-1 MVPUX Research & DesignGrowth & Engagement
"Sure, you guys can redesign planningpoker.com. I'll even give you the URL as long as you keep a free version."- Mike Cohn, Mountain Goat Software
The impact
Thousands of agile teams adopted the rebuilt platform, which remains in active use across distributed and hybrid teams worldwide.
PlanningPoker.com went from a legacy PHP tool with vocal but underserved users to a modern, scalable estimation platform. The redesign launched from a hackathon, earned the blessing of Mountain Goat Software's Mike Cohn, and preserved the trust of a deeply embedded agile community while introducing real improvements that changed how teams plan.
The risk wasn't building it, it was not breaking it
PlanningPoker.com had something most products never earn: genuine loyalty. Agile coaches and dev teams had built their estimation rituals around it for years. The experience was dated and the backend brittle, and distributed teams were working around its limits rather than with them. But the trap in modernizing a beloved tool is obvious in hindsight and easy to walk into: ship a slick new version that loses the thing people loved, and the loyal base that made the tool worth rebuilding is the first to leave.
So the design constraint was continuity, not novelty. I joined as development team coordinator on what started as a hackathon project with no funding and a vocal user base with strong opinions about what had to stay and what could change. Mike Cohn's green light came with one condition, keep a free version, and that constraint, far from limiting us, kept every decision honest about who the tool was for.
We rebuilt the backend in modern JavaScript and APIs for scale, then added only what teams actually needed: card customization, moderator controls, team invites, and session reliability under live pressure. I led user testing with agile coaches and remote teams specifically to confirm we were solving the real friction, not just refreshing the paint, and we held the migration path for existing users open the whole way. Modern enough to win new teams, familiar enough to keep the old ones, is a harder target than either alone.
What this built
- A modern platform with backward-compatible trust. The rebuild kept loyal users while opening the door to new teams that the legacy experience had turned away.
- Product-led growth in a formerly static tool. Analytics, roadmap-based delivery, and clear onboarding paths turned a point-in-time product into something that could evolve.
- Distributed team support at scale. Card customization, invites, and real-time session reliability made the tool genuinely useful for global and hybrid teams, not just co-located ones.
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