TIFFANY CARRELL

Relearning Familiar Tools:
Dropbox Case Study

Dropbox logo

You can't change behavior with tooltips alone.

I worked at Dropbox as the Service Design Manager, then later as Head of Contextual Education. When I joined, most users thought it was just for saving files. The product had grown, but the mental model hadn’t. Decade-long customers didn’t know half of what they were paying for. There was no real education ecosystem, just a help center and some long-form guides buried in the margins. 

So we built from scratch. Not just content, but strategy. Not just one format, but a system of experiments. And not just education, but permission to explore and discover Dropbox all over again.

Why It Matters

Dropbox had always sold itself on “it just works.” In other words, there was no real need for education, much less proactive education and support. But in reality, complexity had crept in and users were getting left behind.

Education became the bridge between product and possibility. This work helped users reconnect with a tool they thought they already knew. It gave them back confidence. And for me, it shifted how I think about education at a foundational level: not as instruction alone, but as reinvention.

The Challenge

Because Dropbox “just worked,” users never had a reason to explore deeper functionality. How might we surface value without condescension, create clarity without overwhelming them, and turn casual users into confident ones through a system that felt more like discovery than correction.

The Big Idea

Dropbox wasn’t hard, it just wasn’t obvious. That coupled with the fact that users didn’t distinguish between help and education meant we stopped trying to force that divide. Instead of only building traditional courses, we focused on "+1 moments" to drive repeated engagement.

My Role

I looked after the service design function within a high-impact, cross-functional team, owning end-to-end responsibilities across product education and program development. That included strategy, content modeling, information architecture, UX, change management, and acting as the connective tissue across product, marketing, and customer success. I was also an internal advocate for user realities and research democratization, pushing the company to rethink what “help” and “learning” even mean in a product like Dropbox.

Guiding Principles

Meet Users Where They Think They Are : Most weren’t beginners, they were experts in their old version of Dropbox. We had to teach sideways, not from scratch.

Is it Help or Education? : Research said users didn't distinguish, so we built experiences that didn’t force users to pick between “learning” and “doing.” By focusing on the job to be done the outcomes got better.

Design for Self-Discovery : Good learning feels like a lightbulb, not a lecture. We made room for the delightful moments, too.

Data-Informed, Human-Led : Analytics gives us the what. Research gives us the why. We design from both.

Reuse, Don't Repeat : Our content model prioritized modularity. Write once, use everywhere... without diluting intent or context.

Deliverables
Massive Impact in Year One

Scaled from 32,000 total visits to 1 million+ in under a year. The system worked because it was built around how people actually learn and wanted to learn, not how companies want to teach.


Modular, Reusable Content System

We built a headless, LMS-agnostic structure. Content became an asset, not a silo. Every touchpoint was a node in a larger learning network. (See image below)


User Research-Driven Strategy

Mapped emotional and cognitive journeys across long-time users, new teams, and admin personas. Reframed our entire instructional model based on how people felt at certain points and phases of their lifecycle, not just what they did.


Multichannel Experiments

Piloted and scaled experiences across formats: live webinars, interactive e-learning, integrated walkthroughs, and standalone tools. Each one was tailored to real user behavior, not just features.


Cross-Functional & Exec Buy-In

Partnered with stakeholders across product, customer experience, customer success, and marketing to build a unified vision for product education. We didn’t just execute, we changed minds.

a screenshot of learn.dropbox.com

Dropbox Learn, the platform we built to host courses, manage webinar registration, and surface tutorials and past recordings in one place.

Contact Me

I'm excited to keep diving into:

Designing for Implicit Learning

How can interfaces themselves become teachers by offering proactive embedded cues, feedback, and nudges that guide behavior without ever needing a step-by-step tutorial?

Rethinking IA for the Headless Era

What does information architecture look like when content isn’t confined to one platform, one surface, or even one moment in the journey?

Blending Emotional and Functional UX

Teaching users by addressing how they feel, not just what they need to know. What if anxiety, confidence, curiosity, and confusion were treated as signals to design for, not just work around?

Ritualizing Discovery in SaaS

Creating repeatable patterns inside the product and workflow that guides people into new features. Not just once, but every time the product evolves.

Education as Experience Architecture

Moving beyond content delivery into intentional experience design where timing, tone, and context are just as important as what’s being taught.

Designing for Legacy Knowledge

Exploring how to unlearn and reorient long-time users with entrenched mental models—treating education as re-mapping, not onboarding.