Revenue Lead Martin Charles lets us in on the challenges and triumphs of leading a brand new, fully distributed sales team

At Dropbox, we kicked off 2020 by expanding our teams in a few new countries and regions. One of these was Canada, where a distributed group based in and around Toronto broke virtual ground on making Dropbox a formidable force in the Canadian tech scene. Revenue Lead Martin Charles gave us a peek into his journey to joining Dropbox in Canada, his distributed leadership style, and his new quarantine hobbies.

What is your role at Dropbox?

I’m the Revenue Lead for Canada.

How long have you been working for Dropbox?

I started in March.

How have you been challenged at work recently?

The biggest challenge I have is leading a remote team, having met them in a remote environment. Everybody has challenges with remote work, but most people knew all of their colleagues and employees before things went down. Your relationships were already solidified, and you had already built trust, so now you’re just migrating to a distributed environment, and it’s just a transition. But for me, it’s not a transition; it’s an inception. I met my direct reports in a remote world. So that will remain the biggest challenge until we get back to some level of normalcy. It’s hard to build trust with people you haven’t met in person, and the most important part of my job (and any manager’s job) is building trust with my employees, period.

What is one thing that’s exciting you about work right now?

One is that we’re new to market. It’s exciting having this huge opportunity to prove ourselves and make a dent, because we’re the first to do it. Because we are a new team, we have an opportunity to not start with bad habits, so making an impact and a name at Dropbox is the most exciting part.

What’s your favorite thing about your role at Dropbox?

I like the idea of being able to flip a switch in somebody’s brain. I have a couple of tenured people who have been in sales in a similar environment for most of their tenure. So for me to be able to offer value from a different lens and have people say, “wow, I never thought about it that way, that’s something I haven’t done for the past seven years that I’m going to start doing now,” — that’s the part I like. I’m motivated by influencing people positively.

What’s one of your favorite Dropbox memories/events?

My interview process. I thought it was pretty thoughtful and involved. It was my best interview experience that I’ve had in my career — and I haven’t had one of those careers where I’ve stayed at the same company for 15 years and another company for another 15. I’ve seen a lot! I’ve been in a lot of interviews, I’ve worked for a lot of different companies, and this was the best experience I’ve had.

Where’s the first place you want to travel when quarantine is over?

Santorini, Greece. I actually had that trip booked for June but had to cancel. So I’m definitely gonna be rescheduling that. I travel a lot — there’s a minimum of like five vacations that must be taken each year!

Are there any new hobbies you’ve been exploring during quarantine?

Podcasting. I was a guest on a couple of them, and then a couple of colleagues and myself started making a podcast about sales, but from a leadership perspective. You hear podcasts from the lens of a sales person, but no one talks about what life is like as a sales leader in a way that doesn’t sound overly professional and PC, so that’s the theme. I also plant now too. Before COVID, I had one plant — now I have 20!

What’s your go-to WFH lunch?

A nice stacked turkey sandwich with fresh onions and basil that I’ve grown, my own fresh hot pepper sauce, and tomatoes and pickles. I use very bougie cheeses and nice bread too.

What’s your favorite thing about working from home?

Sleeping in, not dealing with traffic, and not having to iron.

What would you want prospective new team members to know about working at Dropbox?

You have to know what you want out of the company or the mission you choose to attach yourself to. I like to attach myself to a company that has either pioneered a space or is disrupting a space. Here at Dropbox, we pioneered the space we’re in, but we’re also in the process of disrupting it. Also, if you want to be part of a company that cares about their people, this is the place. The first thing that I could tell here immediately is that this company actually makes decisions in their employees’ best interest.

Think Dropbox might be the perfect fit for you? You can find more information and job postings here.