Inspiring everyday growth with Ryan Cahalane, who transitioned from cultural ambassador on the recruiting team to selling and helping Dropbox business customers

Jul 31, 2018 · 5 min read
Ryan Cahalane

Q: What is your name, what office do you work out of, and how long have you been at Dropbox?

A: My name is Ryan Cahalane, and I’m based out of our New York City office. I’ve been at Dropbox for four years and spent three of them in our San Francisco headquarters.

Q: What is your current role at Dropbox?

A: As an Enterprise Account Executive, I partner with some of the biggest companies on the east coast by selling and helping to deploy Dropbox Business to their employees.

Q: Anything that you have done/accomplished at Dropbox that you’re proud of?

A: I’ve interviewed over 700 people during my time at Dropbox and helped to hire over 40 members of our sales, partnerships, and business strategy teams. It’s been an incredible experience to connect with so many individuals who are passionate about joining Dropbox. As a member of the recruiting team, you’re not only responsible for hiring great people, but also acting as a cultural ambassador for Dropbox as an organization.

Q: Have you had transformational or inspirational moments at Dropbox?

A: I’ve been fortunate to hold a number of roles during my time at Dropbox. The biggest transition for me was moving from the recruiting team to sales where I’ve been for the past two years. Though it’s a different team, there are a lot of similarities between the roles. The same reasons people join Dropbox are often the same reasons organizations buy it. They’re passionate about the product and want to improve how people can work better together.

Q: How did the change come about?

A: The part of recruiting I enjoyed most was when I got the opportunity to sell individuals on why Dropbox was a special place to work. There are a lot of great companies out there, and it was my job to help candidates suss out their professional goals as well as educate them on the opportunities at Dropbox that would hopefully help them realize those goals. A personal goal of mine was further developing this selling motion while also digging deeper into the technical aspects of Dropbox’s product offerings. Having hired much of our sales team at the time and working closely with leadership, I was confident that the revenue organization was the best place for me to do that.

Q: Were you looking?

A: While I wasn’t actively looking to make a move out of recruiting, I was increasingly drawn to the sales organization over time. Having the ability to discuss my goals and career aspirations with members of the sales and recruiting teams was really important to my decision-making process. Knowing I had the support of leaders on both sides was reassuring and a testament to Dropbox’s commitment to helping me, someone who was early in their career, explore the areas I was passionate about growing professionally.

Q: Did someone advocate for you along the way?

A: I was lucky to have a number of advocates, both from the recruiting and revenue organization, who supported my transition. These advocates included my recruiting manager, Melissa Marcus, as well as sales leaders, Jessica Arnold, Kate Taylor, and Jerry Brooner. I had partnered with many of these executives during my time in recruiting, so it was great to have those relationships established as well as a two-year track record of recruiting for their teams to help support my qualifications and candidacy for a role within the sales organization.

Q: Why did you decide to join Dropbox?

A: The personalization of the interview process stood out and set Dropbox apart from any other company I spoke to. I had the opportunity to interview with members all across the recruiting team as well as members of our senior engineering team. This gave me a perspective not only of the team I was interviewing for but Dropbox as a whole. I remember as soon as I received my offer, I was flooded with emails from the recruiting team welcoming me. That level of thoughtfulness and candidate experience was something I knew I wanted to be a part of and contribute to.

The Dropbox New York team on listing day

Q: What surprised you most about Dropbox when you joined?

A: I’ve been most surprised by the level of thought and detail that goes into how decisions are made across the organization. Dropbox has nearly quadrupled in size since I’ve been here yet the amount of focus and attention placed on how these decisions affect employees, teams, and our 500 million users around the world has never changed. It’s this level of thought that inspires me to do my best work and consistently aim higher for my team and Dropbox’s users.

Q: What are your hobbies? Or what can we find you doing outside of work?

A: I try to live an active lifestyle complemented by equal amounts of Food Network. I was a swimmer in college, so the ability to be in the water or gym has always been important to me. When I lived in San Francisco, I got to “Escape From Alcatraz” and swim from the island to the shore. It was a pretty amazing experience, though swimming in the Hudson River does not have the same appeal as the Bay.

Escape from Alcatraz swim in San Francisco

Q: Any accomplishments you’re proud of outside of work?

A: I had never been to California before I moved out to San Francisco for Dropbox. I’m from Sandy Hook, CT, and went to school in Boston, so living across the country for three years is something I’m really proud of. It was a big challenge for me both personally and professionally, but I was fortunate to have support on both coasts from the great friends I met at Dropbox as well as my friends and family back home.

Check back soon to meet more Dropboxers. In the meantime visit us at Dropbox is growing, grow with us!

Life Inside Dropbox

Get to know the people of Dropbox and the stories of how we’re making the world work better. Want to learn more about current opportunities? Check out:


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Dropbox is the world’s first smart workspace that helps people and teams focus on the work that matters.

Life Inside Dropbox

Get to know the people of Dropbox and the stories of how we’re making the world work better. Want to learn more about current opportunities? Check out:

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