Designing a Retention Engine Using Small Groups and Life-changing Transformation for Customers
90 Day Challenge
Context
At Impact Theory, our community-powered learning platforms had a common churn problem: members often dropped off within the first two months, before they had time to build momentum or see real results.
As part of the product and success team, I saw an opportunity to shift from content consumption to meaningful connection.
We needed to give members a clear path, a shared journey, and a demonstrated reason to stick with the program.
Challenge
Traditional onboarding and content delivery left too much to chance. Members were navigating complex personal goals in isolation, and many lost motivation early.
We had no system in place to help them build relationships, feel supported, or celebrate progress with others. Without that emotional connection, retention suffered, and so did customer outcomes.
Below: First round 100 Day Challenge for retention boosting, later changed to 90 Days. Completely built and led high-touch challenge that hosted over 700 people worldwide in localized teams.
Approach
I led the strategy, design, and rollout of the 100-Day Impact Challenge—a structured, gamified, team-based experience that guided members through personal transformation in a deeply human, peer-supported way.
Key features included:
Small teams curated by goal type and time zone, creating built-in accountability and alignment
Weekly mindset prompts, action check-ins, and progress reviews
A clear path from goal-setting to reflection, layered with empathy, community rituals, and celebration
High-emotion experiences that encouraged vulnerability, support, and shared wins
Scalable format built for quarterly cohorts and onboarding flows
Results
Converted a one-time challenge into a repeatable, flagship customer experience
Increased retention from ~2 months to 4+ months
Helped members adopt platform features more naturally and fully by meaningful immersion
Built an ambassador pipeline: top performers became peer leaders, coaches, and community guides
Created bonds that extended beyond the challenge. Some teams are still connected today
Takeaway
People don’t stay because they consume content.
They stay because they feel seen, supported, and connected.
The 100-Day Challenge wasn’t just a retention strategy; it was a relationship engine. It gave people a reason to show up, grow, and stick around.
When customers walk through something hard with others, you don’t just get renewals, you create loyalty for life.
Do Hard Things.
My 4+ years building and pursuing excellence at Impact Theory remain the highlight of my career
so far. The two projects featured here represent only a fraction of what I contributed and learned.
The people I collaborated with challenged me to be relentless in pursuit of results,
and everything I do now is built on that foundation.
Recommendation:
Through her progression from Community Manager to Engagement Strategist to Product Lead, Ambra demonstrated a deep understanding of how to make data-driven decisions while keeping her finger on the pulse of what the customer needs.
- Amy McCarty, Director