Leaders We Admire: Pete Wheelan, CEO, InsideTrack

Artful Leaders

In our ongoing series Leaders We Admire we were excited to talk with Pete Wheelan, CEO at InsideTrack. One of Pete’s leadership strengths is his focus on the importance of enjoying your work, following your dreams and being in the right career. His own career has reflected this, and he reinforces it in his leadership as CEO at InsideTrack. Getting a chance to talk to leaders from various industries is not only a privilege but a great way to learn about how people come to find an industry as well as the joys and challenges they experience in their leadership role. It was an honor to ask Pete Wheelan a few questions and learn more about him as a leader

AL:  How have you decided which roles, industries, and companies to work for?

Pete Wheelan: I always start with what I am passionate about in my life. Not long ago I had a chance to talk to a group of students at Golden Gate University where we discussed this very topic and I like to reference something I call the “magazine and/or cable channel test.” It works like this: Imagine you are stuck at the airport because of a very long layover, so you head over to the the Barnes & Noble Bookstore. Which magazines do you buy to fill your time? Or, maybe you’re home and watching TV. What station or television shows do you find yourself drawn to watching. This is a simple “test” to start identifying the type of work or industries where you can invest your passion. It’s also really important to me to work with quality people and I know that the “sweet spot” is  a combination of what I’m passionate about, the people I work with and something that I’m talented at doing. I like to reference this matrix (on the right) when I’m talking about this topic. When I focus on finding the sweet spot, I may find career opportunities in diverse industries but they allow me to excel and love, enjoy the people I collaborate with and fuel my passion.

AL: Can you name a person who has had a tremendous impact on you as a leader—maybe someone who has been a mentor to you? Why and how did this person impact your life?

Pete Wheelan:  First and foremost would be my father. I know this sounds a bit cliché, but he was the finest example of great work ethic and I learned this from him. We lived in Chicago, Illinois, and my father got up early to work the markets in order to support his family. He was always calm, consistent and fair. Additionally, there have been CEOs that I have worked for in my career that were high quality people and I learned a lot from them. I observed their practices and took away the things that I wanted to replicate. Finally, there have been people behind the scenes who were doing tremendous work and influencing me in a “good to great” type of way.

AL: How would you characterize your leadership style?

Pete Wheelan: Consistent, quietly confident, hardworking and trusting.

AL: What are the most important decisions you make as a leader of your organization?

Pete Wheelan: Building a solid foundation though recruiting, engaging and retaining the best people possible. Once the foundation is built then I must engage and align the people in my organization through setting a clear direction of where we are heading.

AL: Tell me about how you invest in your employees?

Pete Wheelan: Engaging in operational and organizational trust throughout all levels of the organization is critical. We have five office locations (San Francisco, Portland, Denver, Chicago and Nashville) and decided this year that creating flexibility was an investment we wanted to make for our employees. Role clarity is also important. It’s important that each person knows what they need to do to in order to achieve success, and I want to invest in training where there might be gaps or if someone is interested in augmenting their skills.

AL: What is one characteristic that you believe every leader should possess?

Pete Wheelan: Authenticity. Being a leader means that at times you may have to do things that are outside of your comfort level. You may have to be the speaker in the spotlight or you may not be super analytical but you still need to know the data inside and out. Adjusting your comfort level to meet the demands of being a leader will lead to credibility and build trust.

AL: What is the biggest challenge facing you as a leader?

Pete Wheelan: Driving change. For any organization moving quickly, you have to drive change and honor the parts of your past or current present that are foundations—positive and critical—while proactively questioning everything. There are three buckets: things that are working, barely working (working now but not for long) and broken. The middle bucket might mean we have to wait six months to see if something is working. Slow change can be the hardest.

AL: If you weren’t the CEO of a company, what other profession might you be doing?

Pete Wheelan: My wife and I have an ongoing joke that I would be a park ranger if I wasn’t in my current profession. In all seriousness, I probably wouldn’t be a park ranger, but I’m a huge outdoor fan and would probably be a guide for some kind of adventure travel or trip company. It would allow me to continue bering a leader, still being responsible. It would be mentally stimulating. I would be guiding others and ultimately very passionate about it.

Name: Pete Wheelan
Education & College/University: B.A from Dartmouth College, M.B.A from Kellogg Graduate School of Management and a J.D. from Northwestern Law School
Company: InsideTrack
Title: CEO
Number of years with company: 3
Number of Employees total: ~325
Where was your first leadership job? I ran a small valet parking business in high school. My first real corporate leadership role was as Co-founder and CEO of a company called AdventureSeek, an online portal for experiential travel that I started in 1998.
Business book or Ted Talk you recommend to others: The Power of Full Engagement, by Jim Loehr (It’s more of a book about how manage your life and your time, but I think that’s ultimately critical for being a good leader).
Favorite quote if you have one: “Far and away the best prize that life offers is the chance to work hard at work worth doing.” –Theodore Roosevelt

This interview originally appeared on the Artful Leaders Blog, Nov 2015.

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