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Thank you to the 1,400 leaders who’ve generously done the 7 questions!
I hope reading

7 Questions with Steven Benson

helps you in your leadership.



Jonno White

7 Questions with Steven Benson

Name: Steven Benson

Current title: CEO and Co-Founder

Current organization: Badger Maps

Steve Benson is CEO and founder of Badger Maps (, the #1 App in the App Store for outside and field salespeople. After receiving his MBA from Stanford, Steve joined Google, where he became Google Enterprise's Top Sales Executive globally in 2009.

In 2012 Steve founded Badger Maps for outside and field salespeople to upgrade existing CRMs with mapping, routing, and scheduling. He also hosts the Outside Sales Talk ( - a podcast specifically for outside salespeople, and is the President of the Sales Hall of Fame (

7 Questions with Steven Benson


1. What have you found most challenging as a CEO or executive of a large enterprise?

At Badger Maps, we have certainly faced challenges maintaining our company's culture as we have grown. But because we have made this a priority we've been able to open up other offices around the country and around the world and stay true to our culture. We started out with 4 employees in one room, working together and basically at arms reach. The two of those four people who lived in Phoenix when we first started working with them, we moved to San Francisco so we could all be together. When we started hiring remote employees in places like the Philippines and Los Angeles, we kept the culture going by keeping in regular communication with the people who weren't in the room with tools like Slack for quick messages and Google Hangouts for group conferences.

One key thing we have done is have people from the different offices truly get to know one another. When we opened up an office in Spain, one of the original team members moved there. Also, we gave employees from the San Francisco office the option to live and work in Spain for 5 weeks at a time. That way everyone knew each other and had worked in close proximity (and besides who doesn't want to go to Spain). We rented a condo in Spain for them to stay at, and have people overlap in their stay so someone who is on their last week can show the person on their first week around town and make it an easy transition. When we opened up an office in Salt Lake City, one of the original four team members also moved there to start the team. We also send people from the home office out to SLC when we have a new hire, for training and just to get to know one another better.

Another trick we have used is keeping the same 'office hobby' across all the offices. All of the Badger offices have a Foosball table that people enjoy playing - often in a highly competitive manner. Another great thing we've found with Foosball is that it's a really inclusive activity anyone can have fun playing regardless of background, gender, etc. while many office activities tend to feel more exclusive or only some people are comfortable with them. When people go to different offices, they all have this shared hobby in common.

2. How did you become a CEO or executive of a large enterprise? Can you please briefly tell the story?

The short answer to how I became CEO of a large company was that I started a company and then grew it to be a large company. My educational background was a Bachelor of Arts in Geography and International Relations and I followed that with an MBA. Both degrees prepared me in some way for my entrepreneurial journey. I founded Badger Maps, a sales route planner that helps field salespeople optimize their time to get more meetings and sales. Besides having to do with maps and navigation, my undergrad definitely helped me develop my written and verbal communication skills. I believe that the ability to communicate clearly and succinctly is among the most important skills an entrepreneur can possess. Whether you are pitching your company to customers, investors, or setting the direction with the team, this comes up again and again. Another area that was really helpful in my undergrad was learning about diverse perspectives and cultures, because it helped me be more empathetic. Empathy is an underrated business skill.

The MBA was a solid general background for starting my business, because it is broad and not deep or specific and gives general business skills. To start a business, it's important to have a basic level of capabilities in most areas of business, like finance, accounting, sales, marketing, and HR. This is more useful than a deep understanding in one specific area - although that depth would likely be more useful for a more specialized role at a larger company.

3. How do you structure your work days from waking up to going to sleep?

First off, coffee (cold brew is my latest passion) is the secret weapon. Without coffee and tea and chocolate, I truly believe I would have accomplished less than 50% of what I have in life. My routine is to wake up at around 8:45 and walk into the office (eliminating a commute is one of the best parts about entrepreneurship, especially if your commute is to your garage. I live about a mile from work, so my dog and I walk to work in the morning (Badger has a dog friendly office). I’m at the office until around 8 or 8:30pm, then I go home and have dinner and hang out and relax or work out till around 10:30. Then I go back to work till around 3am, then I go to bed.

4. What's the most recent significant leadership lesson you've learned?

I’ve changed my leadership style a lot in the last few years. In business school, we learned to set measurable goals for teams. I used to focus on these numbers, but over the years, I've learned that a great leader needs to focus on hiring, culture, and how to make the team more successful. This isn’t intuitive, but for a growing company, I feel like the main job of a leader is in the HR department - hiring, working to remove roadblocks, teaching and coaching the team.

Being a good leader is less like a high school principal and more like a high school football coach. My leadership style has changed over the years to behave more like a coach, teacher, and mentor. I've always focused on making the people around me more successful, and truly doing my best to enable them along their path on their project, in their role, or in their life. More often than not this helps me and my organization perform at our best.

A great manager doesn't just tell people how to attain the goals, it’s important to encourage an employee to creatively solve a problem. A great coach might say to their pitcher, "I'd like to have less runs scored, how do you think we could approach that problem?" They might think that the answer is in developing new pitches, or it might be in hitting the weights and getting their existing pitches to be faster. But it’s important to incorporate their feedback and thoughts in the solution to the problem, rather than just being prescriptive.

You can still have measurable goals for a team, but what I do is look at the whole group, break it down into its parts, and help coach all the parts to perform better. A great coach breaks down a role, task or skill into parts, and works with you on how you can improve each part. I've learned over the years that success is a team sport - and by being a great teacher and mentor, your team is far more likely to succeed than if you are just managing by the numbers.

5. What's one book that has had a profound impact on your leadership so far? Can you please briefly tell the story of how that book impacted your leadership?

I would recommend that anyone starting a company read The Lean Startup by Eric Ries. You don’t have to join the cult or anything, but it’s worth understanding why there is a cult in the startup community surrounding the philosophies outlined in this book. If you’re starting a SaaS business, read Impossible to Inevitable by Jason Lemkin.

Honestly though, in general the blogs and articles that are relevant to your industry and business model often are a quicker way to attain a ton of background in an area. The SaaStr blog is my favorite.

6. How do you build leadership capacity in a large enterprise?

When leading a team it's important to be a great motivator and help all employees perform at their best. Great leaders are able to help them understand the big picture so they can connect their success back to the success of the business. They are great coaches and show their employees that they care about them, their career, and their future by giving them the information, training, and knowledge to be successful.

7. What is one meaningful story that comes to mind from your time as a CEO or executive of a large enterprise so far?

When I started Badger Maps, there were only 2 people at the company, and we were trying to decide whether we should work from the kitchen table/garage or get some office space. We got some shared office space so that we could have a distraction free environment to work in. Eventually we got our own space, which was a backroom of a dentist office. In terms of the good, bad and the ugly, this was the ugly.

One of the most important things a company needs to do when it’s starting out is to look for great engineers. Good software is hard to build, and you need great engineers to build it. The next step is to start figuring out who the buyers are and talk to them. Even though you don’t have a product to sell, you need to start selling the idea to the people who you think will ultimately buy the product. These conversations help to calibrate your understanding of what’s most important to your prospective customers so you can build the product that they are most likely to buy.

One thing we did well starting the company is make sure that we could cover all the bases across our co-founders. In a startup technology company, you need to be able to build a thing that’s hard to build, and you need to be able to market and sell a thing that’s hard to sell because it’s new. You also need to have someone on the founding team who can truly lead and manage a growing business. A lot of founding teams have some of these skill sets but not all of them. Don't forget that you can always bring on a 3rd founder to bring the skills where you’re weak. It's better to have a small slice of a bigger pie, and usually when you're starting something it's either going to fail or be successful - and covering all the bases greatly increases your chances of being successful.

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