Emily B Flynn

Putting the user first, no matter how technical or novel the software.

My role: Senior Content Specialist for AI and Apple products on the CX team.

About the products: In 2023, Dropbox unveiled a number of new AI features within it’s suite of non-enterprise level products, as well as an AI Control Center. This included dynamic filters, document summaries, translation tools, smart search, search summaries, universal search*, and more.

*Note: Much of what was formerly called Dropbox AI is now under the Dropbox Dash (DBX’s universal search software) umbrella, so my work exists within Dash articles, as well.

About the project: While content around Dropbox’s expansion into AI-driven features existed on a few other surfaces, the primary source of user-facing explanation around how to get, operate, and understand Dropbox AI was in Help Center content.

As the lead writer for AI content on that platform, I was tasked with creating half a dozen articles on these updates, as well as the main content for the new AI Control Center.

Additionally, each new and updated feature required writing several pieces of internal documentation for our customer agents, as well as user-facing email macros (conversational design). These included more detailed technical writing and UX research.

Timeline: From August 2023 – February 2024, I worked closely with the AI product teams, Trust & Security teams, Legal, Comms, Marketing, Design Studio, the Editorial Council, and Executive Leadership to craft high-quality Help Center articles that met users where they are while maintaining complete technical accuracy.

Leadership: As Dropbox AI expanded to encompass more features, including the Dropbox Dash launches, I became the main POC for ensuring UX writing across all AI-powered products and features was consistent. I created a content writer and designer working group which met weekly to discuss product changes, updates from the AI Governance Board, connection to the work being done to update the Dropbox Manual of Style around communicating the in’s and out’s of machine learning features to our direct and enterprise customers, and to make coordinated web and in-app design suggestions. This team consisted of twelve staff across four product teams, reaching senior management level.

Content design in feature development – process and iteration: One of the most essential elements of this project was designing and writing about the AI features On/Off toggle in the AI Control Center. How much conversation can twenty-five people have regarding an On/Off toggle, you ask? How ’bout 4 months worth, twelve design iterations, a few dozen legal reviews, and a Christmas Eve-eve Slack chain with the VP of Communications while she’s in the air and I’m in an airport.

Looney as that sounds, it ultimately was chaotic for the sake of trying to stick to business goals while maintaining the integrity Dropbox users expected.

While leading on the content strategy and development for the Help Center and agent communications, I also consulted and drafted copy for the control center dashboard itself along with the primary AI Content Designer and the Director of Content. I’ve never used the words “toggle” or “sparkle” so much before or since.

In the end, the AI On/Off toggle remained automatically switched “On” for those in the initial beta rounds, the beta rounds were slimmed to accommodate certain concerns which arose from the Community managers and our CX team, and the toggle remained “Off” for those not in the beta. The dashboard was amended with more in-product messaging, more direct links to the AI Policy, and I updated agent conversational design to reflect more nuanced information about AI use across the company.

*Now that most of Dropbox AI has been absorbed into the powerful Dropbox Dash, you can find the progeny of the ethics work around the AI Control Center through the Dropbox Dash Admin Console security features.

Challenges: It seems astonishing to realize that even just a few years ago, AI was not so much a part of our daily conversations as it is today. Having written about AI in direct-to-consumer health tech for several years prior to joining Dropbox, I had some sense already of the anxieties and concerns many of our customers likely shared.

Being part of the CX team meant diving deeply into user’s real struggles and successes with our products by working closely with the talented global agent staff at Dropbox. I brought that user-centric voice of the customer approach to developing the content for this project. I advocated strongly to not sacrifice clear, empathetic, and useful explanations while trying to maintain our typical word count or brand voice.

Dropbox AI product launches weren’t happening in a vacuum, either. At the time, we utilized LLMs from OpenAI, which was facing turbulent media attention as we were rolling out our AI features. Getting swirled in the mix of that PR maelstrom led to my frequent 1:1s with members of the executive suite, often moving at a rapid pace to ensure we were upholding our AI principles and thus earning the trust of our users.

Outcome: Dropbox is a trusted brand because the trust they seek from users is rightfully earned. I can say that with conviction based on my time on these articles.

I’ve never written anything with so much internal scrutiny before or since, but it was worth it. I feel very proud of how much of my advocacy for putting the customer first stayed within the finished articles. The content I wrote reaches millions of viewers every month. Dropbox weathered the PR storms that came along with the very early days of the AI hype, creating products that are useful to their customers and improve their digital routines.

Applying this success elsewhere at Dropbox: I had similar outcomes working with the Apple File Provider and Microsoft Cloud Files teams in my nearly two years with Dropbox. All three of these projects required my senior-level experience with research, SME interviews, SEO analytics, information architecture, and ability to manage ever-changing deadlines and workflows. I wound up mentoring other members of my team who were beginning to work on content with similar technical specifications who needed support around resourcing and content architecture.

Though separate from this AI project, my articles on Dropbox support for macOS on File Provider are on the first page of Google search for “file provider” even without the Dropbox signifier. The primary article had been viewed over 15 million times in the six months leading up to when I left the team. I’m very proud of that work.