Progress Tracking Strategy for BetterUp Manage
From ambiguity to alignment: leading engagement strategy and launches with ✨ AI ✨ as a design partner
When I joined the Manage team at BetterUp, we faced a vague but critical challenge: engagement was dropping off quickly, and managers didn’t have a clear sense of progress after completing a plan.
I led the effort to turn this ambiguity into a clear engagement strategy and shipped improvements that made progress feel tangible for managers. Along the way, I used AI not just as a tool, but as a design partner — accelerating research, generating personas, and helping us move from concept to launch faster.
Making sense of the problem
I began by conducting manager interviews, reviewing behavioral insights, and mapping the bottom funnel journey. These revealed hidden drop-offs: managers were losing momentum before even completing their first plan, and needed more flexibility and variety in their development to stay motivated.
To create clarity for the team, I developed Manage Personas & Storyboards — visual frameworks that showed how different types of managers might engage over a year in Manage.
✨ I innovated by using AI to synthesize research into personas, storyboard realistic journeys, and generate sharper mocks. This approach helped transform abstract concepts into concrete artifacts the team could align around.
Snapshot of Oskar’s journey leveraging AI imagery w/ low fidelity wireframes to illustrate concepts.
Turning strategy into launches
With the strategy in place, I led the design of two launches that made progress visible and motivating for managers.
Personalized goals & insights—surfacing individualized progress cues to encourage repeat plan engagement.
Hypothesis: Showing early signs of growth would motivate managers to complete plans by demonstrating value sooner.
Milestone Celebrations—gave managers recognition at key moments of completion
Hypothesis: Celebrating progress with a personalized, shareable moment would strengthen accomplishment and drive continued engagement.
These weren’t just features — they were the first steps in a broader strategy to make Manage an always-on product for professional growth.
✨ AI also played a role here: I created custom GPTs modeled on personas to run rapid feedback loops and pressure-test concepts and prototypes before launch.
Reflection & impact
What I’m most proud of: leading the strategy that took us from messy ambiguity to a shared vision, and shipping product launches that improved engagement.
This project highlighted my strengths in:
Leading strategy through ambiguity — framing messy problems into actionable direction.
Innovating with AI — leveraging AI to generate personas, accelerate storyboards, and simulate user feedback.
Driving alignment and impact — delivering a vision the team could rally around and tangible improvements for members.
This foundation is now guiding ongoing progress tracking and visualization work across BetterUp’s platform.