Project context
At Dropbox, file sharing serves as a critical viral growth lever, with over 15 million weekly active users performing share actions. As the newly promoted Senior Designer leading this initiative, I spearheaded efforts to enhance collaboration through improved content sharing experiences.
The challenge was significant: users reported frustration with fragmented collaboration tools, while business data indicated a $6.75 million opportunity among teams using multiple workspace tools. Additionally, the existing Slack integration had fallen behind recent brand updates, requiring a comprehensive visual refresh.
Working with cross-functional partners who supported multiple teams, I took ownership of the project strategy, research, feature prioritization, and experience design. Our goal was to meet users where they worked rather than adding to their tab overload, while simultaneously strengthening retention through enhanced integration capabilities.
Challenge
Integrating Dropbox's rich content ecosystem with Slack presented multiple layers of complexity. As I mapped user scenarios and workflows, two critical challenges emerged: content display versatility and permission management.
First, we needed to support Dropbox's diverse content types within Slack's interface constraints. The goal was to create rich, interactive previews that would allow users to take action without leaving Slack. This required careful consideration of display parameters across platforms, including mobile responsiveness and character limits for call-to-action buttons.
The second, more complex challenge involved navigating the intricate permissions landscape between both platforms. Through detailed scenario mapping, I documented the various ways team permissions could be configured across Slack and Dropbox. This thoroughness helped identify edge cases early, allowing us to both prioritize critical scenarios and mitigate potential experience risks. The engineering team particularly valued this comprehensive analysis, as it provided clarity for implementation and highlighted areas where we needed to adjust our scope.
Research Methods
My research approach combined three complementary methods to build a comprehensive understanding of user needs and validate our solutions. First, I analyzed existing research data, which quickly confirmed a significant market opportunity in messaging and chat tool integration, with 30% of users actively using these platforms alongside Dropbox.
To evaluate and refine our solutions, I set up a simulated production environment where our team could test user flows and build empathy with real-world scenarios. This hands-on testing environment proved invaluable for identifying quick wins and prioritizing our roadmap.
Working with our research partner, I implemented a structured dogfooding program with internal Dropbox users who matched our target audience's usage patterns. Through bi-weekly surveys, we tracked satisfaction metrics and gathered detailed feedback on pain points, sharing these insights with leadership through regular reports. This continuous feedback loop helped validate our direction and informed our feature prioritization, ensuring we were addressing the most pressing user needs.
My comprehensive update to the Dropbox Slack app addressed several key user needs, starting with a visual refresh. By modernizing the branding elements, including logo and carousel imagery, we helped users confidently identify our app as Dropbox's official integration. I also revamped the pre-connection homepage to showcase our new features and guide users through installation, working closely with our content designer to craft compelling onboarding messaging.
At the core of the update, I designed richer in-app interactions that allowed users to engage with shared content directly within Slack, significantly reducing the need to switch between applications. This required careful attention to cross-platform compatibility and messaging clarity. Through collaboration with our content designer, we refined our call-to-action language, eventually shifting from "View on Dropbox" to the more versatile "Open" to accommodate various content types, including Google documents.
To enhance the collaborative experience, I introduced view notifications enhanced with emoji, bringing personality to these micro-interactions while keeping users informed of their collaborators' activity. Recognizing that notification fatigue can impact user experience, I also streamlined notification management. The new design offered both granular control and a simple global toggle, allowing users to easily customize their notification preferences from their homepage.
Enhanced preview demo
Impact & Recognition
The project's impact exceeded our initial goals, achieving a remarkable 70% re-adoption rate among dormant users and consistently drawing 700 new app connections weekly. Our connection rate of 0.58% CTR surpassed the standard advertising benchmark of 0.4%, indicating strong user interest in the refreshed integration.
Beyond the metrics, the project delivered several key wins. Our early adopters, primarily Dropbox employees, showed such enthusiasm for the new experience that many disabled other product notifications in favor of the Slack integration. The design system we created was built with scalability in mind, laying groundwork for future integrations with platforms like Microsoft Teams, though resource constraints put that expansion on hold.
Working with a newly assembled team, we maintained lean processes and robust documentation that fostered strong collaboration. This approach not only helped us ship quickly but also enabled us to explore potential expansion across the Dropbox product family, including Capture and Replay. The project demonstrated how thoughtful design and strategic feature prioritization could revitalize a product while building a foundation for future growth.
