Getting Design Involved in Strategy

Getting Design Involved in Strategy

How We Shifted Growth Work From Optimizations to Impactful Projects at Dropbox

The Challenge

In Q2 of 2019, I was leading a Growth team at Dropbox focused on onboarding and marketing. We had three designers serving Growth Managers, and while the work was shipping, it wasn’t hitting the mark. ROI was low, and the designers were becoming demotivated.

The data told the same story: we had hit a ceiling with our optimizations. Moving buttons and running endless A/B tests could only get us so far. Meanwhile, lead meetings and 1:1s made it clear—design wasn’t contributing strategically, and the team’s energy was draining.

My Role

As Design Manager, I needed to ensure that the solutions we shipped were impactful, that the designers on my team were growing, and that we were moving from a service model to embedded, strategic partners.

Resetting the Approach

I started by diagnosing the issues: optimizations weren’t addressing real customer problems, designers were overloaded, and research was limited to evaluation rather than discovery.

From there, I set two principles:
- Reserve time for bigger thinking
- Define problems collaboratively

I aligned with my PM and Engineering partners and shifted our researcher to focus on foundational work. We sponsored a new study to uncover the unmet needs of people who abandoned onboarding. We knew when and where they dropped off—but not why.

In parallel, I invested in usability tooling and process upgrades, and I carved out time for designers to think beyond incremental changes: one designer dedicated 20% of their time to future-focused work, while the other two committed 10% for two quarters.

What We Found

The research came back with striking insights. Half of the people who quit couldn’t identify which product they had tried. Many had landed in the Business SKU when they wanted something simpler—an expensive mismatch that didn’t meet their needs.

Armed with this insight, the designer who had future-focused time proposed a “right-sizing” solution: guiding users to the product that actually fit their needs. That project ran for about a year, reshaping how we matched customers to SKUs. It also spawned related initiatives—upgrade and downgrade flows, and even how we approached subscription cancellation.

The partnership between design and product on that work became a model for collaboration across the org.

The Outcome

By listening to designer sentiment, digging into the data, and sponsoring the right research, we were able to get design involved in strategy in a meaningful way. The designers were more engaged, their contributions grew in impact, and the company benefited from more thoughtful activation and acquisition solutions.

“We knew when and where they quit—but not why.”