At the start of 2021, it became clear that our activation strategy at Dropbox was losing steam. We’d squeezed most of the value we could from generalized onboarding—file, sync, and share alone weren’t enough to keep customers engaged. Something had to change.
Spotting the Opportunity
In a series of working sessions with research, data science, and product partners, we pieced together a bigger picture. The data showed that while many users were getting started, too few were unlocking the deeper value of Dropbox. Our research suggested a new direction: instead of treating all customers the same, we needed to explore targeted activation—different approaches for different types of users.
Making the Case
As the design lead responsible for activation within the Teams SKU, I took on the task of drafting a strategic shift. I’d been thinking about targeted activation for some time, and with the help of a passionate PM partner, we pulled together the supporting data and past research to make the case.
We kicked off strategy discussions with EPD group leads, starting from the top. I proposed a two-track approach: continue generalized activation while dedicating focus to exploring targeted activation. To make that real, I suggested reorganizing our teams around distinct missions.
Not everyone agreed at first. My product partner Frances pushed back on going “all in” too quickly, and rightly so. We landed on a phased rollout: start with one dedicated team, validate the opportunity, and scale from there. Together, we prepared an executive summary of the proposal, which Frances presented to senior leadership.
From Idea to Strategy
The first targeted activation team was formed that quarter. Within a few months, its success justified adding a second team. By the end of the year, four teams were working on targeted activation experiments. What started as a side bet became the foundation for how Dropbox approached activation moving forward.
The lesson: strategy isn’t just about spotting what’s next—it’s about framing the opportunity, building alignment, and pacing the rollout so momentum grows.
What I Took Away
This experience reinforced how design leaders can shape strategy: by connecting insights across functions, making the case with evidence, and helping teams take manageable steps toward a bigger change. Strategy isn’t a one-time declaration; it’s a process of building conviction across the organization.