Dropbox + Slack

Redesigning the sharing ecosystem for enterprise Dropbox users.

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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.

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. ‍