In the most recent episode of Taking The Lead, Challenger CEO Andee Harris sat down with Christina Brady to discuss a number of topics, including the need to create inclusive cultures to embrace people’s unique talents and experiences.  A few of the quick highlights in this article:

  • Equality in the workplace is about more than equal pay. It’s understanding that one person may have more obstacles to overcome than another. We also need to create inclusive cultures to embrace people’s unique talents and experiences.
  • Challenger CEO Andee Harris says changing hiring practices is one way to eliminate unconscious bias. That might mean looking for soft skills instead of requiring certain degrees or focusing on where they were earned. 
  • Andee shares her journey climbing the corporate ladder as well as her thoughts on how women can support each other through “co-elevation” as they seek leadership roles.


Andee Harris might have been among the first Girl Scouts who realized that selling door-to-door was not an efficient sales strategy. Instead, she took her cookie sales to the mall, where she could reach more people. 

More than 35 years later, the Challenger Chief Executive Officer is still thinking outside of the box, not only when it comes to digital sales solutions, but by breaking the glass ceiling and creating more diversity for women in the workplace. 

In an episode of Taking the Lead, Andee shares her journey climbing the corporate ladder (which she says is actually more like a jungle gym), her lessons learned along the way and best practices for hiring, supporting women leaders, and staying aware of unconscious bias. 

Hire outside the box

Andee’s journey to becoming a CEO began at Andersen Consulting, which is now Accenture, in 1999. There, she thought about different ways to work and how to make the business more women-friendly. 

“I’ve always thought a little bit outside the box, or how could I do things better, more efficiently, more inclusively,” said Andee, referring back to her time as a 10-year-old Girl Scout selling cookies at a mall, as her first indication of outside the box thinking — which is now focused among other goals, on changing processes for more inclusive hiring. 

Andee says modifying the processes necessary for change can’t happen overnight, from new job descriptions to looking at soft skills over college education, to increasing diversity among board roles

“We have to just keep fighting. We have to keep working hard to get where we need to be, and we will get there,” she says. “It just takes time and a lot of energy and a lot of people being incredibly passionate and people being willing to be open, to think about things differently.”

Andee is one of those leaders who is dedicated to breaking the glass ceiling, using this outside-of-the-box mentality. She says that process changes might include modifying hiring requirements, such as favoring experiences and strengths over a college degree, or where that degree was earned. She adds that she has fought to change job descriptions so people don’t necessarily need to have an MBA, or four-year degree to take on a leadership role. 

“Not everybody has to have worked at Amazon or Google. I mean, they’re great companies, but let’s think outside the box on how we recruit people,” says Andee. 

“How do we create inclusivity within our organizations and what types of training can we offer so that once we bring people into the organization if they don’t have all of the checkboxes, we can train them ourselves and provide those skills?” 

Hiring people with diverse skills and backgrounds increases inclusivity, and is good for business — especially in sales where connecting with customers is the key to success. Leaders should relate to the people who you are trying to reach, and focusing on diversity can help achieve that.

“We get people who can help us think about how we can relate better to all the customers we’re serving in our communities,” Andee says. “There needs to be diversity in sales because sales is about relationships. If you’re not connecting with your prospect, then you should bring in somebody who does connect with them.”

Stay aware of unconscious bias

One of the biggest barriers to diversity at work is unconscious bias, says Andee: Job descriptions, hiring practices and even people’s networks are rife with it. But hiring diverse talent is just the beginning. Value systems within companies also need to change to help people feel more included at work. 

“It’s more about really helping them assimilate into your organization, be part of your culture … I see it all the time where people recruit great talent but it doesn’t work out,” says Andee. “The biggest reason  is that they didn’t put things in place to make them feel comfortable and to make them feel part of the company’s value system.”

Value systems that include unconscious bias may be entrenched in a workplace, making them difficult to change. 

Andee shares an example: In 1996, when she worked at Andersen, the only female partner in her region went on maternity leave and returned to work three days later. Her colleagues said how “tough” she was. While Andee says a lot has changed in the last 20 years or so, there is still a long way to go toward honoring women for the skills they bring to the workplace.

“We should realize that women bring awesome things to the workplace, and we should embrace that, versus trying to skirt around the issue,” says Andee.  “As women, we’re always trying to calibrate.”

At Challenger — a global sales training, technology and consulting firm — Andee says she focuses on making sure its sales teams are diverse. The question, she says, is how we can continue leveling the playing field for women, not only when it comes to salaries, but roles as well. 

“It’s not just whether the pay is the same,” she adds. “It might be, but women might have a way harder hill to climb. If others have been [at a company] for years and years, they’ve already built a kind of kingdom. So it’s really hard for new people to break in.”

Co-elevate others on the way to the top

Andee says change happens not only by elevating yourself, but others, through sharing your journey and supporting theirs. 

“I’ve been climbing the ladder. I look at it as more of a jungle gym. I’ve gone a little sideways and then back up. We need to have more women leaders. We need to have role models so we can get women promoted to leadership roles,” says Andee. “I’m excited to continue the journey, but most importantly, to get more people on this journey with me.”

Andee teaches a “leading and launching startups” class at Northwestern University’s Kellogg School of Management, where she aims to mentor women who are focused on improving diversity, women’s health, women’s initiatives and women’s empowerment. She focuses on shared values to inspire other women to think outside the box. 

Says Andee: “I can’t always understand where people are coming from, but once you’ve lived an experience, you really have shared values.”

This article is based on an episode of Sales Assembly’s podcast, Taking The Lead, which features top female B2B Tech Revenue Leaders, VCs, Advisors, and Icons. Bi-weekly episodes dive into a tactical topic to help listeners (regardless of gender or seniority level) learn how to be better, faster, and smarter as they navigate the craziness of the Revenue world within B2B Tech.