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Daily Challenges 2.0

Diagnosed a customer support spike as a product design flaw, not a messaging issue. Reprioritized the 2.0 roadmap to first introduce campaign sunsetting logic, then redesigned the feature as a tiered progression system.

Skillz Senior PM, Engagement 2025 3 months
+10% D14 retention
+5% Net revenue

Context

Daily Challenges was a core retention mechanic at Skillz. Customer Support reported a high volume of complaints: users experienced abrupt challenge resets from Day 7 back to Day 1, which they perceived as a product bug and a loss of progress. This was damaging trust in the feature.

Approach

  • Investigated cross-functionally with Marketing and identified that challenges were being replaced mid-cycle to keep content seasonal, but the system had no sunsetting or graceful completion logic.
  • Recognized this as a product design flaw, not a communications issue. Proactively paused and reprioritized the broader 2.0 roadmap to first introduce proper campaign sunsetting and completion logic.
  • Ensured users could finish in-progress challenges even when new campaigns launched, before moving to the broader 2.0 redesign.
  • Redesigned Daily Challenges as a two-tier framework: short-term daily goals unlocking long-term rewards, creating a cohesive progression with variable rewards.

Result

  • Eliminated the primary source of Daily Challenges complaints and restored user trust.
  • 10% improvement in D14 retention.
  • 5% increase in net revenue.
  • Formalized lifecycle management for Daily Challenges as a sustainable product, not just a campaign.