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Driven & Co. Ep: 24 – One Man’s Journey from Sales to Successful Entrepreneur

Steve Benson, Founder and CEO of Badger Maps, talks with host Justin Gray about his 12+ years in sales, how mobility sparked the idea for his company and whether he thinks he’s made it –– all on the the latest episode of Driven & Co.

Plus, scroll down to learn how to receive free access to Badger Maps for two months!


Tell us about Badger Maps and give us a window into your role as CEO.

Badger Maps offers field sales people a mobile, map-based solution, enabling users to sell more in their territories. I spend a lot of my time working with our team and helping them be the best they can be, thinking about what we need to do next, who we need to hire next and actually going through the process of finding the right people for those roles.

You started out as a sales professional, correct?

My whole background was in field sales so I was very familiar with the problems that we were trying to solve when we set out to address the routing, scheduling and organizational challenges a field sales person comes up against.

What did you want to be when you grew up?

I always kind of drawn toward business and sales and profit. I started what I would call a distribution business – selling fireworks to kids in my junior high. The fireworks were not legal in Illinois at the time but I could order fireworks from Indiana by mail and then I could sell them for 1000% margins. There were some risks in the business, like someone blowing off their fingers, but I never actually had anything bad happen. My parents would wonder why I had so many random guys from my junior high swinging by the house for 10 minutes at a time.

How did you ultimately get into sales? What was your first sales job?

My undergrad was in environment international relations and I focused my second major in environmental geography. I got an MBA for grad school. Right after college I was at Allstate and then I went to IBM right after business school to work in sales.

How did you come up with the idea for Badger Maps?

Our origin story is that I had the problems that Badger Maps has set out to solve. Things like understanding what a territory looks like, where are my best customers and what customers are the most important in a particular geographic area.

I had experienced these questions firsthand. Because I was working at Google at the time, I was exposed to the switch to a mobile world. I knew I had these problems and could see that cloud computing, mobility, ubiquitous internet connectivity and mapping were all going to come together. I knew they would allow us to create a solution of this nature to solve these problems that I had, knowing also that a lot of other sales people had them too. That was where Badger came from. I was in the right place at the right time and saw those trends coming together.

What were big surprises you experienced moving into the role of CEO?

There’s a lot of moving the chess pieces around on the board. It’s a lot more strategic and a lot less tactical. Sales is inherently tactical and hands on, and there’s a lot more strategy and a lot more HR than I would have guessed or was prepared for.

Has there been anything that helped prepare you for that transition? Have you had any mentors along the way that you would point to?

One resource that stands out for me is Jason Lemkin. During the first two years of the SaaStr blog, he was able to address a lot of the challenges that you face through a lot of the phases of a business. He explained, “Oh, when you see this happen and this happen, go do this.” And, “Do this and here’s why, and here’s what happens if you do it the other way.”

Do you have a definition of making it? Have you ever felt like you’ve reached that point, or have you thought about when that will be?

There’s lots of different levels of making it, right? Creating a business that survives, solves problems and that people are paying for – that’s making it to some degree. Then scaling that business and hiring a bunch of people is another level. Then eventually exiting the business is another level and there’s 10 more levels in between.

Making it means different things for different people. I’m personally not super money motivated, so for me it’s more about the journey and more about impacting employees’ lives and growing them as people. There’s financial, professional, personal, and growth goals, and you want to make it in all of them.

To find out more about Steve Benson and his journey to becoming an entrepreneur, click here to listen to the entire interview. Connect with Steve on LinkedIn and Twitter. Plus, visit badgermapping.com. Mention “Driven & Co.” when you sign up, and they’ll throw in two months free!

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