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Andee Harris of ‘Challenger’: “Know your worth!”

To quote my 2021 vision board, “Know your worth!” As women, we tend to underestimate our value or think that we are just part of a diversity plan. I no longer approach salary negotiations and equity discussions from a place of scarcity, but a place of abundance. In my first board role, I did not […]

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To quote my 2021 vision board, “Know your worth!” As women, we tend to underestimate our value or think that we are just part of a diversity plan. I no longer approach salary negotiations and equity discussions from a place of scarcity, but a place of abundance. In my first board role, I did not even ask for equity or payment; I was just honored that they would give little old female me a board seat! I did not value my time, network and all the things I have invested in my career. That is no longer the case.


As a part of our series about strong women leaders, we had the pleasure of interviewing Andee Harris.

Andee Harris is the newly appointed CEO of Challenger. A proven leader, Harris brings more than two decades of experience in growing and scaling service and technology businesses. She has previously led multiple companies, both as CEO and Senior Vice President, through periods of rapid revenue growth, critical fundraising and successful acquisition. These companies include Highground (acquired by Vista Equity Partners), TMBC (acquired by ADP), Syndio and Emerging Solutions (acquired by Emtec).


Thank you so much for joining us in this interview series! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your “backstory”? What led you to this particular career path?

I owe it all to Girl Scout cookies. No, seriously. At 10 years old, with all the frustration a cookie-dealing Girl Scout could muster, I knew there had to be a more efficient alternative than peddling sweets door-to-door. At the time, my dad was an entrepreneur and early executive at The Limited. I started tagging along with him on the weekends and took my cookie-selling operation to the middle of the action: the mall. I would set up a little stand outside of the store and talk to all of the customers. I came back each Saturday, and it paid off: in 1983, I sold the most Girl Scout cookies in the country! The seeds of hustling, working hard, and always innovating were planted, and they have stayed with me since.

Can you share the most interesting story that happened to you since you began leading your company?

Three weeks into my new role as the CEO of Arlington-Virginia-based Challenger, the United States Capitol came under siege. As our headquarters is only a few miles away from the Capitol building, my immediate priority was to ensure all employees in the area were safe. I also wanted to make sure Challenger’s stance on the matter was clear — we condemn the acts of violence and unrest in D.C. and support and uphold the principles of democracy. Fresh in my new role, I not only wanted to be a strong leader for my company during this time, but also a leader in our community.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

Fresh out of college, I moved to Chicago and worked for Andersen Consulting (now Accenture). A couple of years into my entry-level job at a gigantic corporation, I felt I had seen enough to declare to my boss that their entire business model sucked. Though I was only 26 years old at the time, I took note that the company had zero female partners and felt it did not operate a friendly, sustainable model for working parents (both moms and dads). Of course, my concerns weren’t taken seriously, and I eventually ended up leaving and starting my own consulting firm that did afford equal opportunities to our employees. We ended up winning Best Company to Work for in Chicago for many years. So, while I may look back and laugh at bold, empowered 26 year-old me, I’m proud of standing up for inequality from a young age, and now as a CEO, I make a point to listen to the concerns of all employees — whether they’ve been at the company for one year or 50 years.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

My dad taught me valuable business (and life) lessons during my formative years. He taught me how to sell, how to have confidence in my abilities, and how to believe in myself and my accomplishments no matter my age, class or gender. Additionally, throughout my career there have been so many influential people who have supported me and helped me along the way. I really believe in having a “Personal Board of Directors” — a collection of people who know you really well and can give you good insights and advice. My board always holds me accountable and helps me stick to my core values. If you don’t already have one, I highly recommend creating a personal board of your own!

In my work, I often talk about how to release and relieve stress. As a busy leader, what do you do to prepare your mind and body before a stressful or high stakes meeting, talk, or decision? Can you share a story or some examples?

Of course, I go through the typical preparations before a high-stakes meeting — exercising, deep breathing, cranking up some motivational music. But my secret weapon is channeling my daughter. She always tells me she believes in me and is proud of me, and I try to channel that energy when I’m preparing for something big or beginning to feel any tinge of self-doubt.

As you know, the United States is currently facing a very important self-reckoning about race, diversity, equality and inclusion. This may be obvious to you, but it will be helpful to spell this out. Can you articulate to our readers a few reasons why it is so important for a business or organization to have a diverse executive team?

I believe that diversity of thought is extremely important to have on an executive team. When you have a diverse team, you get different mindsets and experiences and can then make better choices for the direction of the company and your employees. I recently watched novelist Chimamanda Adichie’s TED Talk where she speaks about the danger of a single story — how if we only hear a single story about another person, country, race, etc., we risk critical misunderstandings. This is the importance of having diverse groups, teams, employees at an organization. We must hear everyone’s voices and everyone’s stories.

As a business leader, can you please share a few steps we must take to truly create an inclusive, representative, and equitable society? Kindly share a story or example for each.

I think we need to be more cognizant of the small, unconscious actions and decisions companies sometimes make. Years ago, when I was the CMO for a company that acquired my business, the executives would go on an annual retreat at a hunting lodge. No one ever bothered to note that the hunting lodge was for males only. A few days before the retreat, a fellow (male) executive informed me that I would not be able to attend for that reason, but not to worry — someone would take notes for me and share them upon the males’ return! Of course, I thought the proposal was absolutely ridiculous because I, an executive, needed to be able to attend the executive retreat. The retreat location was ultimately changed, but the idea that my male counterparts thought it was okay for me to just “catch up” with them when they returned really struck me. These are the types of small, insensible acts that organizations (and individuals who run organizations) must change in order to create a more inclusive environment and workplace.

Another step I think companies must take is to change job descriptions in order to meet the needs of a more diverse workforce. For example, is it really necessary for most professional jobs to require a four-year college degree? Maybe this is vital in some roles, but I don’t think it’s necessary if you have 20 years of work experience or other experiences that are just as relevant. Small changes and modifications like this would instantly appeal to a more diverse group of candidates.

Ok, thank you for that. Let’s now jump to the primary focus of our interview. Most of our readers — in fact, most people — think they have a pretty good idea of what a CEO or executive does. But in just a few words can you explain what an executive does that is different from the responsibilities of the other leaders?

Good CEOs co-elevate. That is, they elevate everyone around them and help them grow, while also holding them accountable to that growth and making sure they are working together as a team. As CEOs, it’s also our job to focus on the future of the company. While the employees hold the fort together, our job is to look ahead and see where we need to go.

What are the “myths” that you would like to dispel about being a CEO or executive. Can you explain what you mean?

One of the most frustrating myths of being a CEO is the whole idea that you have to lead with authority. In a command-and-control model, you can’t be compassionate, empathetic or soft. And if you are soft, then you can’t make tough decisions. In one of my previous roles as CEO, they told me that they were initially hesitant to hire me because they thought I was too nice and wouldn’t be able to make tough decisions. It’s such a shame that there’s this idea that a CEO needs to be some tough, number-crunching boss, when I’ve actually found that more empathetic individuals are much better leaders.

In your opinion, what are the biggest challenges faced by women executives that aren’t typically faced by their male counterparts?

Throughout my career, I’ve faced a lot of challenges on the investment side of business. It’s really hard to raise money and to get promoted as quickly as men. When I interview for board positions, I don’t have the same experiences as men. Women are just catching up to our male counterparts, and we need to continue to be role models for each other.

That being said, for as many disadvantages that women may have in the workplace, there are many advantages as well. I have a group of women (who serve on my aforementioned Personal Board of Directors), and we have all been supportive of each other throughout our careers. I also think that during the COVID pandemic, female leaders have been able to express more empathy and compassion to their teams, where male leaders may have lacked those traits.

I have also been working from home while my two children have been going to school virtually. While it’s been hard, I am thankful that I am able to do both. I know this hasn’t been an option for all mothers throughout this pandemic, and many of them have had to take time off to take care of their children and become teachers. I do worry about this as a potential setback for women, but I’m hopeful there will be a positive outcome.

What is the most striking difference between your actual job and how you thought the job would be?

Having been a new CEO before, one of the biggest things I look forward to when I start my new role is meeting the rest of the executive team in person and visiting all of the company offices. With COVID cases still surging, I haven’t been able to do that yet. It’s been a bummer because I value in-person interactions. Luckily for technology, I’m able to meet everyone virtually and still meet with my team members one-on-one, just in a different way than expected.

Certainly, not everyone is cut out to be an executive. In your opinion, which specific traits increase the likelihood that a person will be a successful executive and what type of person should avoid aspiring to be an executive? Can you explain what you mean?

I believe that the top traits for a successful executive are (in this order): purpose and passion, optimism and resiliency, a questioning mindset, bias for action, and networking and selling skills. Traits I believe are not suitable for a successful executive? Individuals who lack a growth mindset, are not open to learning, do not have a bias to action, and look at life with a “glass half empty” lens.

What advice would you give to other women leaders to help their team to thrive?

I’ve always believed in setting a good example for other women, especially in the workplace. For example, if I ever need to leave work early for my children’s doctors’ appointments or soccer practice pick-ups, I make sure I let that be known. I never want other mothers at our company to feel that they need to hide their mom duties because they are afraid of how it looks to others. We should never have to worry about motherhood coming in the way of our careers, but rather embrace motherhood and being a leader.

How have you used your success to make the world a better place?

At least once a year, I angel invest in women-owned startups. Each start up I choose is focused on wellness for women and/or helping mothers in the workplace. Some of examples of my recent investments are Bonfire and Lil Gourmets — I highly recommend everyone check them out!

What are your “5 Things I Wish Someone Told Me Before I Started” and why? (Please share a story or example for each.)

1)It can be lonely at the top. You don’t just get to be one of the team; you have to give people space to do things without you, and you cannot be everyone’s best friend at work. I acknowledge this and lean on my YPO forum and women’s leadership group for support.

2) Imposter Syndrome is real. Even when you have had multiple successes, you always second guess yourself and wonder if you’re the right person for the job. In my past two positions, I replaced male CEOs who had been with the businesses from the beginning and were very knowledgeable about the business and the industry. I had to remind myself that the board brought me in for a reason, and I played to my strengths.

3) This one has taken me the longest to learn– you will not be everybody’s cup of tea, and that’s okay. The more authentic you can be with who you are, the more comfortable you’ll feel being yourself. I remember the first time I got a negative review on Glassdoor; it nearly broke me. I cried for hours and wondered how I could fix it. The reality is that someone just did not like me…and that’s okay. If you try to be everything to everybody, you’ll be exhausted and will still not win some people over.

4) I love the idea of not dimming your light to make others feel better. I used to use self-deprecating humor as a way to make men feel better and more comfortable, and now, I just let myself shine and try not overanalyze situations . This one only took me 40+ years to master!

5) To quote my 2021 vision board, “Know your worth!” As women, we tend to underestimate our value or think that we are just part of a diversity plan. I no longer approach salary negotiations and equity discussions from a place of scarcity, but a place of abundance. In my first board role, I did not even ask for equity or payment; I was just honored that they would give little old female me a board seat! I did not value my time, network and all the things I have invested in my career. That is no longer the case.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good for the greatest number of people, what would that be? You never know what your idea can trigger.

Two movements come to mind. First, I think there should be a greater focus on supporting entrepreneurs from diverse communities. There are brilliant leaders and entrepreneurs in the world, and for them to get support to help them succeed would be not only life-changing for them, but beneficial for the rest of us!

Second, we need to rethink high school education and start including real-world learning. For example, when my son started his internship, he had no idea how to write a business email. If we could teach our children about personal finance, business best practices, and other life skills, they would far more prepared to enter the real world.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

My favorite phrase is, “Don’t get furious; get curious.” It reminds me to try and learn from every situation. A field hockey coach told me this when I was 15 years-old, and it has stuck with me ever since.

We are very blessed that some very prominent names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them

In November 2018, Stacey Abrams lost the election for the governor of Georgia by a margin of less than two percent. Rather than hang up her hat and walk away, she chose to rise up and fight for the inequalities that caused her to lose in the first place, namely fighting voter suppression. Now, thanks to her tireless campaigning, Abrams has become a powerful symbol of hope, fairness and equality across America. She started a grassroots organization that she had to build from the ground up and did not have anyone hand her anything. All of this to say, I would love to grab a bite and chat with Stacey Abrams!

Thank you for these fantastic insights. We greatly appreciate the time you spent on this.

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