Breaking Out of Incrementalism
The Challenge
When I first joined Dropbox, I inherited a small team of three ICs working on Onboarding. They were in the middle of a transition—from acting as a service arm to PM partners toward becoming embedded in squads. The problem was that they weren’t able to get ahead of the work.
Instead of shaping strategy, they were shipping small optimizations: moving a button here, tweaking a flow there, A/B testing everything. The work was revenue-generating, but the quality and impact of solutions were starting to degrade. Watching this pattern, I realized we were heading in the wrong direction.
My Role
As Design Director, it was my responsibility to make sure the solutions were not only good but impactful. I also needed to motivate the team by giving them meaningful problems to solve—not just incremental tasks handed down from PMs.
Resetting the Strategy
I started by analyzing the reality of the situation: why were we stuck in small optimizations? My conclusion was that the team lacked a clear process to shape bigger opportunities.
So I drafted a strategy framework:
1. Draft → Identify opportunities and outline hypotheses.
2. Align → Partner with PMs and stakeholders to ensure we were chasing the right goals.
3. Iterate and Refine → Explore multiple design directions, not just one.
4. Validate → Run concept testing with users to confirm value early.
5. Execute → Deliver solutions with confidence that they mattered.
I socialized this approach with PM partners, showing them how a more strategic design process could still serve business needs while unlocking bigger opportunities.
The Results
The shift was significant. By validating ideas earlier and aligning on impact, we moved away from low-leverage optimizations toward more meaningful improvements in onboarding.
Designers felt more motivated because they were working on problems that mattered. PMs became more engaged partners, excited to test concepts and understand user value rather than just running button-placement experiments.
In short, we traded “moving buttons” for solving real onboarding challenges—and design’s impact grew noticeably.
“Small optimizations keep you busy. Validating value makes you impactful.”
Key Lessons
- Incremental work is a signal—it shows when process is broken.
- A clear framework creates space for bigger, more strategic solutions.
- Concept testing turns vague opportunities into validated problems.
- Aligning with PMs is critical to shifting from service work to strategic partnership.