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Meet Roger Benson: The Fast Interview

Roger Benson, Vice President of Sales (Growth) at Fast

Roger Benson

Role: Vice President, Sales (Growth)

Team: Sales

Why did you join Fast?

It was really important to me after spending such a long time at Yelp, it was important to me to find another company with great culture and a clear mission, but also a company that was building a product I felt I could describe to people in simple terms: It’s one-click checkout.

What were you doing before Fast?

My first job out of college was at Lehman Brothers, which is famous for one of the largest bankruptcies ever. I thought I was set for the next 10 years. That gave me a lot of perspective, which was a huge advantage. When I joined Yelp as an entry-level sales rep making cold calls, I had “the grass is not greener'' mentality that gave me much thicker skin and a higher tolerance for pain. I decided as long as the lights are on I'm gonna find a way to be successful here, and I'm not going anywhere until I do.

Where did you grow up, and what were you like as a kid?

I grew up in a town called Plainview, which is on Long Island in New York. As a kid, I was outgoing but awkward. I had two big brothers who were incredible athletes and these amazing role models. And I just couldn't keep up. Then, all at once in one year, I went from being this tiny nugget to entering high school 6’1” and 150 pounds.

What accomplishment are you most proud of?

I’m pretty psyched about my relationship with my wife. I’m proud to have landed in a partnership that is so meaningful, successful, and awesome. And the culmination of that are these kids that we’ve made. I don’t know if there’s anything even close to that. She and I both work full time, and being able to support each other as equal partners is super important to us.

What’s your productivity hack?

When I have energy and feel creative or like I could be productive, I lean into that and I won't stop until it runs out. On the other side of that coin, if I don't feel like I have it, I lean into that too.

When did someone's kindness toward you make a big difference in your life?

Early on in my sales journey, I was not successful. Out of my class of 12, I would put myself square at the bottom in terms of figuring it all out and actually delivering meaningful results. And this guy, Paul, who was in charge at the office I worked out of, for what felt like no good reason, just decided that he was going to help. He decided that he was going to make a project out of me and invested real time and energy into helping me improve. His kindness was pivotal in my choice to pursue leadership as a career so that I could have the same impact on others that he had on me.

Living or dead, who would you like to interview and why?

Barack Obama is always the first name that comes to mind. If it was two people at the same time, it'd be Barack Obama and Jay Z. I think they would play well off each other.

Who is your celebrity doppelgänger?

The one I’ve gotten the most is Alan Ruck.

What is your top travel destination?

If I could go anywhere on earth tomorrow, I would probably spend that time eating sushi in Japan.

Where do you see yourself in a year from now?

We just had a baby, so I assume I will be in my new house we just bought in New Jersey with my slightly bigger family. I'm going to be a very proud father of a beautiful little girl, and a year from now she’ll be running around the house with her older brother. And I'm super, super excited about that journey. That's going to be a ton of fun.