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  • story – 10 min read
  • AUDIO – 28 min listen

AI for the people

Scaling content across customer experience,

marketing, and design at Dropbox

A conversation with Rachel Calabretta, Kate Pluth, and Angelique Little

Writer-using orgs at Dropbox
What led
you to start looking at AI solutions?
Why did you choose Writer?
What advice would you give other industry leaders?

Listen to the Dropbox story or read the (edited) story below.

Writer is the full-stack generative AI platform for enterprises. We empower your entire organization to accelerate growth, increase productivity, and ensure compliance.

Writer transforms work by delivering high-quality outputs that are accurate, compliant, and on-brand. Our platform consists of Writer-built LLMs, a Knowledge Graph that connects our models to your internal data sources, AI guardrails to enforce your rules, a flexible application layer, and an ecosystem of robust APIs and integrations. Our enterprise-grade platform doesn’t use your data in model training and complies with SOC 2 Type II, HIPAA, PCI, GDPR, and Privacy Shield.

Kate Pluth is the Head of Content Strategy at Dropbox, where she leads the marketing content team that spearheads efforts across web content strategy, customer stories, and integrated marketing.

Angelique Little, Content Design Lead at Dropbox, works to create a simple, cohesive, and trustworthy user experience across every touchpoint in the Dropbox product and throughout the organization.

Rachel Calabretta, Manager of CX Scaled Content Development at Dropbox, has over 10 years of experience developing and managing programs to create a learning-centric environment.

All three are members of the Dropbox Editorial Council, an internal organization responsible for developing, enforcing, and maintaining content guidelines and best practices. 

Read or listen to the story of how Angelique, Kate, and Rachel and the Dropbox team use Writer to increase writer productivity, equip non-writers to contribute excellent content, and ensure brand compliance across the organization.

Tell us about the genesis of the Dropbox Editorial Council and how it’s evolved.

Angelique Little

When I joined the company, the Editorial Council had gone through 3 or 4 leaders in the past year. The most recent had left the company and I was asked to chair it with Charles Bohannon, who was on the customer experience (CX) team.

We set about shoring up the guidelines primarily, but also trying to pull in new people. We wanted it to encompass the whole company. We revamped how meetings went to minimize debate about terms and do most of that async, so we could do more knowledge sharing. We then came up with the idea to have leads so that we could have people from across the company participate in the leadership so it wasn’t just the two of us doing everything. That’s how Kate got on board. And then I think pretty early on, Kate identified Writer as an option for us and we started investigating it. And it fit our idea of having guidelines accessible to everyone.

Our internal tagline about Writer was to “bring the guidelines to the people.” The problem we were having is that the guidelines were just this passive document in Dropbox that people would have to remember existed and then go check, and people just weren’t doing it. Even writers weren’t doing it. We were constantly having to remind people that there were guidelines. So we thought if we could bring guidelines to people where they’re working, then we wouldn’t have to do that effort of constantly telling people that there are guidelines, or having people ping us about the guidelines. Let’s get them out there and make them public. And so we thought Writer would be a great way to do that.

Home of Dropbox customer success stories
Home of Dropbox customer success stories

What led you to look at AI products?

Angelique Little

Early on, there was a commitment when our CEO, Drew Houston, made an announcement saying, “We’re going to be an AI-first company. I want everyone to be thinking about how we can be using AI.” Kate and I were already pretty deep into evaluating Writer. Kate was really driving the timing of it to make sure that we could get ahead of the wave so that it would carry us to success.

I had posted a poll in one of our AI Slack channels asking how many hours a week people were writing, how often they were blocked by writing, and whether they were aware of our guidelines. Overwhelmingly, people said they were spending four to six hours a week writing. This was across the whole company and that they that had to overcome blockers about 50% of the time. Basically, people were like, “When can we have [Writer]?” Having that kind of support, too, helped us make the case for adopting an AI solution.

“We don’t need all the technical jargon. We want a more friendly, conversational language.”

Rachel Calabretta

Rachel Calabretta
Manager CX Scaled Content Development

Rachel Calabretta

In CX, our leadership was also gung-ho about AI. Around the beginning of the year, our leadership told us they wanted to be at the forefront of it. They saw a lot of areas in the things that we do — not just us on the writing side of things, but in our quality analytics team, and even in agent support interactions.

We knew that a lot of what we were doing was going to be powered by AI, and we started digging in a little more to see what tools were out there specifically for content development. We learned that Kate was starting a POC with Writer. It was the perfect storm of everybody doing some research into what was out there.

Pretty much everybody on my writing team and a couple of members of my training team are members of the Editorial Council, so we all had that shared goal of common writing language, common writing style, and continuity across the board.

For us, we had obviously some very specific needs. We write for very different audiences, consumption and support, so we needed to be able to make the switch between those two languages. We don’t need all the technical jargon. We want a more friendly, conversational language, and we need to be able to write concisely with a little more heart. Being able to switch between those two languages was something that was very important for us when we were scoping our project and defining our goals.

Why did you choose Writer? 

Kate Pluth

We had a lot of needs, but I think we can narrow it down to a couple of big ones. The first is what we’ve been talking about: writing guidelines and bringing them to the people. We have the nitty gritty details that we want to bring to people‌ and so having a tool that would give us the control to say, “No, we’re sentence case, and this is our word list and terminology.” The added benefit of Writer is that it also checks for inclusivity, which really matters to Dropbox, as we have a whole inclusive language guidelines.

The second piece was about generative AI. There were a lot of tools that had some of the writing guideline-oriented features, but didn’t also have generative AI capabilities. [Another issue] was trying to find something where it’s not going to be hallucinating claims that we aren’t comfortable with. We wanted to have some level of control on the templating and prompt crafting to make sure that the output was at a level of quality that we were happy with.

The next piece is really all about security. Writer has its own LLM that allows for enhanced security and privacy, which was an important factor when Dropbox was evaluating the platform. Every step of the way with the evaluation, we had a lot of very savvy people saying, “Okay, but there’s a lot of great stuff about this, but is it going to train on our data? How does it handle our data? What level of data you are going to be using this for?”


Knowing that a lot of the other tools out there are built on top of third-party LLMs, that was something nice about Writer: it has its own LLM that’s proprietary. We all get to have a lot more control over how data is handled and where it’s stored.

The kicker was recognizing that a lot of the tools out there are really geared toward marketing and marketing use cases, which is fine for me, but I knew that if we were going to be adopting something more, that we wanted to get more value out of it across other organizations.

That’s why I really appreciated being able to work on this with Rachel and Angelique to get the perspective of how other people will use it. Is it something that you could put in a Help Center?

And then there are other things: our IT department wants to have single sign-on and admin controls, and because we’re an enterprise, we need to think about how we control permissions.

Suddenly, you have a really long list of requirements. Once you start ticking all those boxes, there aren’t that many solutions out there.

“We thought if we could bring guidelines to people where they’re working, then we wouldn’t have to constantly tell people that there are guidelines.”

Angelique Little

Angelique Little
Content Designer

You recently integrated all of your products into a single platform. Some things must have gotten pretty hard on the content front! 

Angelique Little

The number of complex terminology decisions has rapidly increased over the last year at Dropbox, even throughout this launch the past three to six months.

This really highlighted an issue we’ve been dealing with for the last year: people are developing terms and there’s no visibility into the fact it’s happening and people are already having to use those terms because everything is happening so quickly. You’re constantly incurring content debt because things are going out into the world that are not correct and you know that the guidelines exist but those people either didn’t get them in time or you couldn’t get them into your database in time.

Writer can now show people that there are guidelines so that if they don’t see a guideline, they can say, “Hey, where’s the guideline for X because it should be here,” or being able to put in Writer that it’s a pending term so people at least know it’s being worked on, and they can ask if they need some clarification.

The Dropbox Help Center
Rachel Calabretta

I’ve always been the lead of the internal content teams and training, and then in April a couple of years ago, I inherited the Help Center as well, which opened my eyes to all kinds of things. We — admittedly very loosely on the internal side — followed the Dropbox Manual of Style and Writing Guidelines because there was this veil of security that it’s not external. Nobody is going to see it, but you’re going to talk about it. You’re going to speak to customers at some point and how we write definitely impacts how we speak about it. So if there’s a term that’s been de-branded and we’re still writing about it internally, we’re still talking about it to customers because it’s still there in our internal content.

So something that was really, really important to me was being able to change the way that we speak internally, so that it is continuous with what’s going on in the company and all the external content. Otherwise, we’re shooting ourselves in the foot because we’re still saying the wrong things or using the wrong terms and not speaking the way that Dropbox speaks and it seems very disjointed to customers.

“We need to punch above our weight. Generative AI is a way for our writers to be more efficient and scale their expertise”

Kate Pluth

Kate Pluth
Head of Content Strategy

What are some of the challenges that you hoped AI would solve?

Kate Pluth

One is ‌consistency and quality. We have a lot of people in marketing — who may not be professional writers — who chip in on public-facing content. There are writers on my team, and we also work with agencies. I want to empower them. It’s all about scale and consistency for me.

We need to bring a lot of marketers along the way, and know that our team alone cannot write every single word that gets published on our website or goes into a campaign.

We have some very ambitious marketing goals that we need to hit and content plays a role in a lot of that. Right now, I do have a very nimble writing team, and we need to punch above our weight. Generative AI is a way to help us scale in that way to get us more efficient with our processes, to save even on agency costs. These are all things on the table that we’ve been considering over the last year. We are‌ on the front foot of figuring that out ourselves, because I don’t want to wait for someone to tell me how I should do it.

“People were like, 

‘When can we have [Writer]?’”

Angelique Little

Angelique Little
Content Designer

What are some of your favorite use cases with Writer?

Kate Pluth

The most straightforward one is automating as much of the proofreading as we can. Especially if we know that a lot of our style guide is pretty straightforward and is catching, for example, that we use the serial comma and we use sentence case. Being able to find that and fix it with a click is awesome.

We are also working with Writer to build custom apps for SEO content, which is a repeatable, regular rhythm of content that we are producing and optimizing. That custom app is just getting off the ground now, and we’re already seeing ways that even just the magic links feature in Writer can help us with the link-building and internal linking that we need to do across the site. We have a person who looks after all of the publishing in our content management system on our web team, and she’s really excited to now have Writer at her disposal to speed up QA.

There are lots of ways that we’re getting excited to think about not just how we use generative AI to create something that’s new, but also to repurpose content and ideas that we already have.

The other thing we use Writer for is ad copy and being able to produce lots of different variants and get them out in the market and be able to try and see what sticks.

Using an SEO optimization custom app in Writer

How has your team responded to the adoption of AI?

Kate Pluth

Where I’ve started is my writing and content studio team. I want to get it in the hands of people who really know what good looks like first and make sure that they know how to use it and how they want to incorporate it into their workflow before we put it into the hands of people who aren’t professional writers.

One of our lead writers has been taking the lead on thinking about not only what those guidelines are for us, but also how to roll it out to the rest of marketing. I have to hand it to him because he’s started his workflow in a really different way, where he says, “For everything that hits my desk, I’m going to try with Writer.” He’s discovering that there are ways that it can be part of the creative process in a really fruitful way and help speed up the things for which you might otherwise be banging your head against your desk.

Angelique Little

There’s a designer on my team who has dyslexia and has trouble writing and spelling sometimes. We’ve actually had a couple of instances where I would say something about his writing and he would get very defensive because he felt criticized. And so I asked him to be my design advocate for Writer. He’s been playing with it and using it in advance of everyone else using it, and he’s Slacking me, you know, like, “This is a game changer. This is literally changing my life.” 

What advice would you give other leaders who want to build AI into their workflows?

Kate Pluth

For now, I’d say it’s a balance of control and speed. We want to make sure that folks who do have the most expertise and are closest to what good looks like can iron out some of the practices first and then be able to scale it. But then at the same time, we know that other people are going to find use cases that we might not have thought of, and we want to let people play and get it in their hands.

But people also want peace of mind, and want to know they are using a tool that we know is secure. With Writer, we got an education on how LLMs work, how our data is used, and we definitely did our fair share of reading security white papers.

Rachel Calabretta

We created a safe space for those who wanted to play and experiment, but also created baby steps for people who were a little more timid about using AI in general, or had some anxiety about trusting AI to help with their work. We created a training and onboarding process that will [eventually] get us to full generative adoption. We said, “Here’s what it can do. Feel free to go in and play and experiment and try things.” And if you’re not there yet, “try this first, try this next.”

What are you all most looking forward to in the future at Dropbox?

Rachel Calabretta

I’m looking forward to the future with multi-product and being a multi-product platform. I think we know that’s going to lend itself to all kinds of changes in processes and the way that my team works, and we’re going to have to do a little more strategy on our operations. Part of that is AI and implementing tools like Writer that we’re exploring for other various areas, but I think it all stems from the multi-product platform that Dropbox is moving towards.

Angelique Little

My vision for Editorial Council when I took it over like a year and a half ago was to bring all the writers at Dropbox together. We are scattered, probably in 12 different orgs, so we don’t have any central leadership. There’s no easy way to bring us all together. It’s been a slow process, but we have three leads from different organizations on this call who were actively involved in bringing this pilot together. I’m looking forward to Writer continuing to unite us and make the dream a reality.

Kate and I are both working on initiatives to use content more systematically with modules and reusing content for consistency. I’m trying to connect the dots to the future of how AI is going to help us personalize content experiences on the fly. Writer is the first step in that journey.


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