ASK THE QUESTION, TAKE THE CHANCE

Some of us take time to find our footing as we venture into the working world. Some hit the ground running. Andee Harris is firmly among the latter. The CEO of Challenger, which empowers sellers and drives sales growth around the globe through sales training, technology, and consulting, hasn’t missed a beat since earning her B.A. in organizational studies and human resource management from the University of Michigan. “I started out as a psychology major and realized that this didn’t speak to what I wanted to study, so I created my own major. I was never a kid who colored inside the lines, and what helped me bring my career into focus was to think of it not as a ladder but as a jungle gym. There are a lot of paths to play on.”

Harris began her career at Andersen Consulting (now Accenture) where she traveled constantly, working 70 to 80 hours a week. She learned a lot, but within a few years was ready for something different. “My experience at Andersen helped me realize that I was going to be happiest if I pursued roles that allowed me to use my rebellious, curious nature to solve problems and make businesses better,” she explains. “I saw I had a comfort with risk, so I began taking strategic risks for the right opportunity, particularly for businesses at an inflection point.”

At 26, Harris co-founded the software services firm Emerging Solutions, which was later acquired by Emtec Inc. for $30 million. She went on to serve as CEO of HighGround, a software company, which she successfully sold to Vista Equity Partners in Harris was named as one of the city’s most successful technology entrepreneurs by Crain’s Chicago Business and nominated by Illinois Technology Association as a Prominent Woman in Tech in 2015, 2016, and 2017. After HighGround, she founded the private equity firm Franklin Heritage. “Launching your own business versus taking over an existing company is like building from scratch rather than remodeling a house,” Harris relates. “If you nail the mission, the vision, and the product market fit at the beginning, you nail your company’s success and culture. But there’s a lot of joy in guiding an existing business through cultural change, just like there is when you’re remodeling and you figure out how to make that one weird load-bearing beam work in your new layout.”

At Challenger, Harris, who lives in Lincoln Square with her husband, Jonathan Harris (director of the Team to End AIDS) and their two college-age children, works to increase the firm’s market share and revenue, while assuring that its clients receive the most sophisticated, multi-pronged guidance to realize their own success. “Companies come to us when they need to help sellers, marketers, and any other revenue pros learn how to challenge customers to improve and grow, align their entire go-to-market team, and create structure and reinforcement so that this approach to sales is really embedded in their day-to-day work. Challenger isn’t a one-and-done training program. It’s an encompassing, strategic approach to growing business and deepening the connection between customers and sellers as trusted advisors.”

Harris’ natural tendency to ask “why not?” and her extensive experience have allowed her to assess business realities from many angles and help clients recalibrate their perceptions. “Businesses are so focused on return on investment or ROI, and I don’t want to diminish the importance of ROI, but they really need to shift their focus to the cost of inaction or COI. Research found that as much as 80 percent of deals end in no decision, meaning people choose to do nothing rather than make a change. So, as sellers, it’s important to emphasize not what you’ll gain by investing in a new solution or approach, but what you’ll lose by not acting. Because there are often bigger costs to staying the same than committing to change.”

While her business savvy has certainly been shaped by her years at the top, like many leaders, Harris has taken to heart life’s early lessons. “When I played field hockey,” she recalls, “one of my coaches offered me advice that guides me to this day: ‘Don’t get furious, get curious. When you see something you don’t like, ask questions. Learn about your options, and what works and what doesn’t. Dig into the problem and find a new path that solves the problems you see.’ I took that mentality into my first business, and I maintain it even now.”