Photo by Dan Stroud

Hilary McQuaide on telling the Dropbox story

Communications team lead Hilary shares her path from politics to venture capitalism to technology and tells us what she loves about her role.

What team are you on, and what do you do at Dropbox?

I’m on the Communications team, which means I get to spend my days telling stories about the products we build, the cool ways that our customers use those products, and the people that make Dropbox such an awesome company.

During your career, you’ve transitioned from working in politics, to venture capitalism, to technology . What inspired each step?

I was a diehard political science major in college. I spent several years interning for my congressman and enrolled in just about every political science class Yale offered because I just knew what my path was going to be. I have two bookcases full of my favorite books on political theory and US politics, and I watched West Wing religiously, of course.

After college, I decided to try something completely different for just one year before law school (the natural step to a career in politics of course), so I dabbled in the world of tech by working at a venture capital firm. I loved it so much that my one year turned into nearly five! I found it fascinating to look at what made certain companies more successful than others and how the tiniest inkling of an idea could grow into something that could change the lives of millions of people.

My decision to move into a tech company was born from that — I didn’t want to just look on anymore, I wanted to be involved in the teamwork and process of making one of those ideas successful. Not everyone has to be actually building that product to play a role. I’m thrilled that there’s a really cool role for me, which is telling the story of what teams are building and why what they’re building matters.

Why did you decide to join Dropbox?

In choosing where to work, the most important thing for me is that I have to believe in and understand the power of the product. In one form or another, working in communications means I’m basically talking every day about why people’s lives will be made better because of that product! That doesn’t mean I have to be the target audience for the product, but it sure does help when that aligns. I was an avid Dropbox user before I joined and am even more so now. It’s invigorating to be able to represent a product that hundreds of millions of people around the world use, and love too — the appeal is pretty universal.

“It’s invigorating to be able to represent a product that hundreds of millions of people around the world use, and love too — the appeal is pretty universal.”

Leadership and people are also incredibly important factors, because that makes or breaks the working environment and the future of a company. Everyone I met during the interview process impressed and challenged me, and the first thing I noticed from each person was how overwhelmingly passionate they were about Dropbox and their role. That is so inspiring, and working here now, I can say that I feel lucky every day to be surrounded by an incredible, talented group of people who are truly committed and who I am constantly able to learn from.

What surprised you about Dropbox when you joined?

My first week of work, I was walking down the street wearing a Dropbox t-shirt and two total strangers pointed and said, “Oh, I love Dropbox!” That’s one way to make you feel great about your decision to join.

I was also astounded by how big of a footprint Dropbox had for such a small team. You hear about company size versus user numbers all the time, but on my first day I walked around the office (half of which was empty space “to grow into”) so that I could meet and introduce myself to every person by name. At the same time we reached 100 million users. The dichotomy there was so incredible.

Hilary and the Dropbox Sydney team during a trip Hilary made to the Sydney office.

What, in your view, is unique about doing communications at Dropbox?

There are lots of things that are special about communications at Dropbox. For one thing, there’s always something (or, 18 somethings) going on at the same time — never a dull moment! That keeps it exciting, and it’s a healthy challenge to be thinking along a bunch of different lines at once. We’re also in this incredible time where the company is growing really fast, but our team is comparatively small — so everyone has the opportunity to be involved in a lot of areas. For example, we’ve set up shop in three new countries in less than a year without having anyone solely assigned to international PR. And there’s a never-ending list of things we’d like to be able to work on but just haven’t had the time for yet. So this a great place to be if you want to be able to build up expertise in one area of communications but also get the chance to dabble in a bunch of other related things too.

What do you enjoy most about your role, and what is most challenging?

One of the best things about being on the communications team is that you get to work with so many people from across the company. This is particularly awesome at Dropbox where every person you work with has something insightful, new, or different to offer.

Personally, my favorite part of the job itself is working on the messaging and narrative that goes with a new product or feature. I really enjoy bringing together all the various pieces of the story that we use to explain why this thing matters and how it’s going to make life better for our users.

“I really enjoy bringing together all the various pieces of the story that we use to explain why this thing matters and how it’s going to make life better for our users.”

In terms of challenges, I’d say one of our biggest right now has been figuring out how to scale the communications team. There’s so much awesome stuff going on here, and there’s always more that we want to be able to do — we just need a few more hours in the day.

What are the top things you have learnt during your time at Dropbox?

  • People make or break a job (here, they make it).
  • There’s always going to be more that you want to do or that you could do, but sometimes prioritization is key.

What have been some of your favorite moments at Dropbox so far?

I really love product launches. They can be incredibly hectic, there can be lots of pressure, there are a bunch of questions to answer and a thousand things to sort through, but it’s just such an amazing feeling when so many people across the company come to together to make something happen for our users. Then after all this we finally get to pull the curtains off to show the world. Soon after the launch we start hearing gratitude and amazing feedback from our users, and the team here can take a deep breath and be like, “Wow — we built that and made it happen.” It’s really, really exciting.

The last half of 2014 was super exciting because our product team was simply on a roll. All these cool things they’d been building all came together week after week and we were able to keep introducing new things to users. The marketing and communications teams were on marathon pace, and the sales and user operations teams kept passing along thanks from the customers they work with who were excited about all the new capabilities we were bringing them. At the end of it the various teams got together to be like, “Did we really just pull all that off?” That was probably one of my favorite moments at Dropbox. We were so busy during those months but it was exciting and collaborative and really, really rewarding — and that makes it all worth it.

What is something that many people don’t know about you?

Outside of work, I have an alter-ego — I teach tap dance classes. I grew up performing and started teaching and choreographing while at Yale. For several years after that I spent just about all my spare time performing in musical theater productions and choreographing high school musicals. My favorite shows that I’ve performed in include The Producers, 42nd Street, Singin’ in the Rain, Crazy For You, Will Rogers’ Follies, Joseph & The Amazing Technicolor Dreamcoat, and Seven Brides for Seven Brothers. Teaching lets me stay just a little bit involved in that world!

Hilary and her fellow dancers rehearsing the “Be my guest” segment for their Beauty and the Beast performance.

If you weren’t doing communications at a tech company, what would you be doing and why?

I see myself working in tech for a long time — it’s a fun, fast-paced, ever-changing area to do communications, and I love the way it keeps you on your toes.

Dream job after all this? Well this may come as a surprise to no one, but someday I’d love to do communications for the San Francisco Giants. Haha!

How would you describe Dropbox in 3 words?

I’d say that working at Dropbox is inspiring, intense, and invigorating. All of which makes it super rewarding!


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