What 4 Colorado CEOs learned from their first jobs

by Jess Ryan
February 15, 2016

Every CEO got their start somewhere. From flipping burgers as a teenager to running a paper route, there’s a lesson to be learned from the jobs that kick off careers. We spoke with some of Colorado’s top CEOs about their first jobs, the lessons they learned, and how the gigs shaped their paths to CEO.

Alan Sage,

What was your first job?

My first job was working at the Taco John’s on Arapahoe in Boulder across from Boulder High School. I started there when I was a sophomore. At the time, the store was the highest grossing location in the chain. The owners had a devout focus on customer service and a strong sales mentality.

What lessons did that job teach you?

I started out making tacos but was quickly promoted to the cash register. It was a sales job at the core, and I started learning about the connections between selling, customer service and revenue. Small upsells added up over the day and resulted in higher revenues and more happy customers. It taught me about the different roles needed in any business, on a micro scale. You have to make a great product in order to stay in business and keep customers, but product isn’t enough, there has to be a sales function to help customers make decisions. And of course marketing to get them in the door, and accounting to track financial progress and set future goals.

How did it shape your path to CEO and make you a better leader?

This foundation of customer service has remained with me throughout my career, so I guess serving Boulder High students trained me well in that regard! Digabit is a SaaS company, and our customers are not just buying software from us, but investing in a shared business solution that they know we’ll keep doing our best to improve. I try to have as much personal contact with customers and potential customers as I can, not so much with the idea of selling in mind but mostly to listen and get feedback on their business problems. When you’re selling a piece of software that you hope the customer will use for the next five to ten years, it’s a little different than a taco, but the principle of understanding a customer’s needs is exactly the same.

Patrick Quinlan,

What was your first job?

My first job was mowing lawns for my neighbors when I was in 7th grade.

What lessons did that job teach you?

Do it right the first time! This is something my father taught me. One night I was in bed asleep when my dad noticed I’d done a poor job so he woke me up and made me edge the lawn in the dark while he held a flashlight.

How did it shape your path to CEO and make you a better leader?

Acquiring each new customer was something I loved and was much more fulfilling than actually mowing the lawns. I realized I wanted a team to handle the details so I could look at the big picture, and the experience taught me how difficult those details can be.

Matt Steinfort, 

What was your first job?

I worked at Arby's washing pots and pans for a summer in Johnson City, New York when I was 16.

What lessons did that job teach you?

Biggest lesson I learned was how very differently various people thought about and approached their jobs. Being my first job, and given I have always been pretty competitive, I was super gung ho on doing whatever I could and was driven to work hard and figure out how I could help (even though that meant cleaning out the grease trap with my bare hand and a fountain soda cup - yuck!).  I assumed everyone would approach their jobs with the same mentality, had the same intrinsic motivations. Instead I saw more peers and even supervisors whose motivation and commitment levels included "punching the clock" or"raging against the machine" than I saw those with a lot of passion or enthusiasm. I also learned you can't get the smell of grease from shaved meat droppings out of polyester pants.

How did it shape your path to CEO and make you a better leader?

This first job and the lesson I learned about people's varying levels of motivation definitely shaped my path to CEO and my leadership style on a couple of fronts. First, I quickly learned that I wanted to find a career and work for companies where I was surrounded by as many motivated people as possible, those that shared my level of enthusiasm and passion, where everyone had a high bar for their personal and the team's performance. Second, and this has been a longer and harder lesson that I'm still reminded of every day, I have learned that no matter where you work and what team you are on, there are always going to be people with different levels of motivation and commitment. As a CEO, I've realized that one of my primary responsibilities is not just to surround myself with people that are naturally motivated (although that would be nice), it is also to figure out what motivates people with different priorities and perspectives, and then to put them in a position where they can be excited, successful and impactful.

Marc Braunstein,

What was your first job?

My first job was as a Biochemistry Laboratory Manager at the National Institutes of Health (NIH) in Bethesda, Maryland. I was 21 years old.

What lessons did that job teach you?

It taught me what it was like to work in the government system. I was unfulfilled by both the pace and lack of creativity, so much so that I realized that I needed to reinvent myself. I went back to school and earned my MBA from Wharton. After that, I landed a job at a Fortune 100 company and started my career in business.

How did it shape your path to CEO and make you a better leader?

In business and as a CEO, you understand that reinvention is part of the game. I started a direct mail catalog company in 1986. We reinvented ShopAtHome.com in the early 2000s and, today, we’re a leading eCommerce company in our space. Reinvention is critical. Fear of reinvention is fatal.

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