Career Stories: A Chat with Steve Dool, Depop's Director of Brand Marketing

Welcome to Careers Stories! Follow this series, where we’ll hear from Depop folks at various stages of their career journey, as we shine a light on how they reached their version of success – and the people that helped them along the way. This week, we're chatting with Steve Dool, Depop’s Director of Brand and Marketing: 

Your First Job

My first job right out of university was as an assistant to a Managing Director at a New York PR agency on their crisis communications team. That was a hell of a way to enter the workforce—a lot of my 23 year old self negotiating with people who seemed to exist in perpetual panic, both internally and externally. But, as intense as it felt at the time, I still call upon a lot of the competencies I honed there: striving for clear communication; developing a coherent strategy in response to a roadblock; building coalitions and consensus efficiently; and trusting my instincts when I don’t have the luxury of time. It also definitely helped me learn how to remain relatively chill when people around me are spiralling, which comes in handy both personally and professionally. Identifying and developing those transferable skills has paid dividends. (Can you tell I also worked in financial PR?)

Your Career Path

It seems adorable now to look back at my younger self feeling anything approaching “burnt out” after a big 12 months of working, but working in crisis comms was tough, and more importantly, it was not in service of something I felt especially passionate about. The types of clients who sought my team’s skills (banks, real estate developers and the government) left me feeling a bit cold. I always had an interest in fashion, though, and eventually found my way to a small but influential fashion consultancy who needed a communications specialist. It seemed profound to me at the time, but it was really just adhering to the simplest advice that so many people give so frequently: if you have the opportunity to work in an industry or discipline that genuinely interests you outside of work, it makes a world of difference in terms of satisfaction and motivation, and probably in your progression, too. And so I’ve been schlepping through the fashion world in some capacity ever since.

Your Squiggly Career

I went from PR to fashion consultant to journalist to magazine editor to Depop. I wish I could say I had a grand plan, but the through-line that has guided each move has simply been a willingness to explore what interests me and to seize opportunities as they arise. I studied journalism in school and loved it, but didn’t write a single thing professionally for most of my 20s because I felt like I had made a decision about a different career path and therefore had to see that through. And I wasn’t totally fulfilled for that reason. Then, one day, I ran into a friend who worked at The New York Times and for whatever reason in the moment I felt bold enough to tell him that I wanted to write style stories on the side. He agreed to let me start with some small assignments for the Styles section, literally for $25 a pop. But I put a lot into it, and that led to more substantive work at the Times, which then led to writing for all sorts of other publications, from CNN to GQ to Vanity Fair, and to eventually writing my book (available at finer booksellers everywhere). So, if I had just stayed in what I thought was my lane, I would probably still be in that lane. 

Your Career Pivot

Pivoting from PR to journalism full-time was a relatively smooth transition in terms of skill set, as they both rely heavily on writing and crafting compelling narratives. But, it definitely came with challenges in terms of earning the respect of my peers.

Some fashion editors are wary of fully embracing PR people, and especially when I was a freelance journalist who wasn’t attached to a staff position at a magazine, I was on the receiving end of some pretty dismissive behaviour. It was a lot of feeling like my peers didn’t take me seriously at first for making a leap that isn’t a super common path. That was one motivating factor that led me to accept a role as Style Editor at Complex Magazine—the feeling that I needed professional validation and legitimacy from someone else.

Looking back, I don’t think I actually needed that validation at all to achieve what I did, and it was the last time I made a career decision based on pleasing someone else. I ended up loving the Complex job, though, and I got through those moments of feeling like an outsider by focusing on doing good work, reminding myself to believe in my ability, tuning out the noise and schmoozing the hell out of people who didn’t previously want to give me the time of day. (Mixed results on that last one.)

One other thing to say about career pivots, in general—including internal moves—is to make sure you’re assessing your current opportunity and new options honestly and critically. No matter what your job is, there can always be an idea that the grass is greener somewhere else, and often a little buyer’s remorse after you make a move.

No job is perfect, and potential perks can be seductive, but it’s the day-to-day motivation, satisfaction and purpose found in your work that will affect you most in the long term. Going to glamorous events all over the world when I was a fashion editor was fun and gives me something punchy to talk about when there’s a lull in the conversation at a boring dinner party, but it doesn’t compare to the feeling of seeing how projects I’ve built in partnership with our colleagues here have made tangible differences in Depop sellers’ or creatives’ lives or helped change the consumption habits of so many people for the better.

Figuring out what gives you purpose and pursuing that will get you through the stressful days a lot easier than anything else.

Why Depop?

I arrived at Depop because I had previously worked with someone in New York who was doing some light consulting for the team there, and she sent me a job listing and encouraged me to apply.

I knew a bit about Depop already, as resale apps were picking up speed at the time (I had also desperately tried and failed to sell a rag & bone coat on another marketplace site that I impulse bought at the Barneys warehouse sale, so had done a little sniffing around about other, newer resale platforms). I was convinced that it was worth the risk joining a company at the start of their growth journey. And I’m glad I was, because here we are, five happy and fruitful years later, and I am so proud to be a long-serving team member here.  

Closing Thoughts 

I am very grateful that Depop has allowed me to do a lot of things I might not have been able to bring to fruition at other companies. My first role at Depop was to come in and develop a structure and strategy for our influencer workstream.

When I joined, we had one woman in New York working very hard to onboard a ton of influencers there, and Oskar Platts-Palmer (Senior Marketing Manager) making great strides in London getting talent involved when he had extra time on top of his regular responsibilities. It was a fun challenge to work with Poppy Russell (Senior Brand Partnerships Manager), who was also a new joiner on the team at the time, to try to make sense of how we could work with influencers and demonstrate their impact based on our objectives then. And then, I got to do it all again when we launched our Brand Partnerships function at the end of 2019.

The fact that we managed to get collaborations up and running with Adidas and Richard Quinn and Netflix and Samsung with quite literally zero budget for two full, calendar years was pretty wild in retrospect. It was our scrappy, start-up mentality that allowed us to seek out innovative tactics to get projects off the ground then, and that way of thinking is still being adapted in our current reality to push the business forward in new and exciting ways.

It’s a great holdover from the early Depop days, and I’m really glad that the culture here, as I’ve experienced it, is one that values innovation and creativity. As someone who has worked at companies of all types, I can confidently say that is something that makes Depop very special.

This is going to sound mad corny (apologies), but the truth is I have four steadfast aspirations for myself within the company: 1.) Continue pushing forward alongside my extremely talented colleagues in the Marketing Org to serve our community and bring Depop to more people than ever before. 2.) Avoid making the same mistakes twice (only new ones allowed). 3.) Soak up as many insights as can be gleaned from all of the cross-functional teams here who have insane skill sets and experience—and try to do the same in return when I can; and 4.) Maintain a youthful enough appearance so attendees at our IRL events don’t think I’m an undercover cop. I’m a young millennial, for God’s sake!!!!