Andee Harris is a name that resonates with success and innovation in the tech industry. As the CEO of Challenger, she has consistently demonstrated her prowess in transforming businesses and driving exponential growth.
With over two decades of experience, Andee’s journey is a testament to her unwavering determination and exceptional leadership skills.
Her impressive track record includes leading several companies through rapid revenue growth, critical fundraising, and successful acquisitions.
Companies like HighGround, TMBC, Syndio, and Emerging Solutions have all flourished under her leadership.
Harris’s ability to connect data and people sets her apart as a rightbrain thinker in a left-brain world.
From Girl Scout to Business Mogul
Entrepreneurial spirit began at a young age for Andee.
“I owe it all to Girl Scout cookies,” she says. At ten, she knew there had to be a more efficient way to sell cookies than going door-to-door. Inspired by her father, an entrepreneur and early executive at The Limited, she set up shop at the mall.
Her strategy paid off, and in 1983, she sold the most Girl Scout cookies in the country. This early success planted the seeds of hustling, hard work, and innovation that have stayed with her since.
Leading Challenger to New Heights
At Challenger, a sales training and enablement platform, Harris’s leadership has been pivotal.
Challenger focuses on transforming sales organizations by equipping them with the skills and insights needed to win in complex sales environments.
Her vision and strategic direction have driven Challenger to become a market leader, helping businesses navigate the challenges of modern sales landscapes.
Additionally, she hosts the podcast “Winning the Challenger Sale,” which has more than 100 episodes where she shares expert insights and actionable advice on mastering the Challenger Sale techniques and driving sales success.
A Baptism by Fire
Just three weeks into her role as CEO of Challenger, in January 2021, the United States Capitol came under siege.
With headquarters only a few miles away, Harris’s immediate priority was the safety of her employees. She ensured Challenger’s stance was clear: condemning the violence and upholding democracy.
This early test of her leadership showcased her commitment to her team and her community, solidifying her role as a strong and principled leader.
A Proven Track Record
Before Challenger, Andee’s leadership was instrumental in the success of HighGround, a company she led to one of Chicago’s largest tech exits in 2018.
As CEO, she spearheaded initiatives that transformed HighGround into a leader in employee engagement software, ultimately leading to its acquisition by Vista Equity Partners.
Her tenure at TMBC and Syndio further solidified her reputation as a transformative leader.
At TMBC, she played a crucial role in the company’s acquisition by ADP, and at Syndio, she was the driving force behind its rebranding and market repositioning as a people analytics powerhouse.
Learning from Mistakes
Harris’s path to success was not without its humorous missteps. Fresh out of college, she boldly declared to her boss at Andersen Consulting (now Accenture) that their entire business model was flawed.
At just 26, she noticed the lack of female partners and the unsustainable model for working parents.
Though her concerns were dismissed, this experience led her to start her own consulting firm, which later won Best Company to Work for in Chicago.
This early stand against inequality shaped her inclusive leadership style.
A Thought Leader in Technology
In addition to being a business leader, Andee Harris is also a respected thought leader in the technology space. As an Adjunct Professor at Kellogg School of Management, she shares her entrepreneurial wisdom with the next generation of leaders.
Her course, Launching and Leading Startups, is highly regarded for its practical insights and actionable strategies.
Her involvement with prestigious organizations such as the Forbes Business Council, YPO Chicago, and various boards, including Bonfire, Chicago Ideas Week, Lyft Community Board, and The Lurie Children’s Hospital Strategic Founders Board, underscores her influence and commitment to making a positive impact.
Harris’s role at Kellogg is a reflection of her passion for teaching and mentorship.
She believes in empowering others through knowledge and experience. “Strong leadership starts with your mindset,” she often says, emphasizing the importance of mental resilience and strategic thinking in leadership.
Championing Diversity and Inclusion
A vocal advocate for diversity in the workplace, Andee brings a passionate commitment to fostering inclusivity. She believes that diverse executive teams bring varied mindsets and experiences, leading to better decision-making.
Inspired by Chimamanda Adichie’s TED Talk on the danger of a single story, Harris emphasizes the importance of hearing all voices and stories within an organization. Her efforts to create inclusive environments are evident in her actions.
From challenging exclusive executive retreats to advocating for job description changes to appeal to a more diverse workforce, Andee Harris leads by example.
Throughout her career, Andee has benefited from having a “Personal Board of Directors” — a group of trusted advisors who provide insights and hold her accountable.
This concept, she believes, is crucial for personal and professional growth. “If you don’t already have one, I highly recommend creating a personal board of your own,” she advises.
Managing Stress and Finding Balance
Harris prepares for high-stakes meetings with a combination of exercise, deep breathing, and motivational music. However, her secret weapon is channeling her daughter’s unwavering belief in her. This personal touch helps her combat self-doubt and approach challenges with confidence.
Looking ahead, her vision for the future is clear. She aims to continue driving innovation and growth at Challenger, expanding its reach and impact in the sales training industry.
Her focus on leveraging data and technology to empower sales teams is poised to transform the way businesses approach sales and customer engagement.
Her commitment to mentoring and teaching the next generation of leaders remains unwavering.
Through her work at Kellogg and her involvement in various boards and councils, Harris is dedicated to shaping a better future for the tech industry and beyond.
Quotes from a Leader
Harris’s words of wisdom resonate with many. “To succeed, you need to be adaptable and open to change,” she says, highlighting the importance of flexibility in today’s fast-paced business environment.
Her insights into leadership and innovation are widely respected, making her a sought-after speaker and advisor.
Her advice to aspiring entrepreneurs is simple yet profound: “Believe in your vision, but be willing to pivot when necessary. The path to success is rarely a straight line.”
This pragmatic approach is a hallmark of her leadership style and a key factor in her success. Andee Harris’s journey is a story of relentless pursuit of excellence and innovation.
From leading high-growth tech companies to mentoring the next generation of leaders, her impact is both profound and far-reaching.
Her blend of strategic vision, innovative thinking, and unwavering commitment to growth makes her a remarkable leader.
This interview was originally published on ValiantCEO.
