Women Of The C-Suite: Debra Fleenor of Adapex On The Five Things You Need To Succeed As A Senior Executive

An Interview With Ming Zhao

Go with your gut. Trust your intuition. Our mind puts out a lot of noise, but our guts lead us in the right direction. Our gut holds years of accumulated experiences and wisdom. Trust in it. This is particularly important for women as we tend to have less confidence in ourselves than men. Don’t give into the imposter syndrome. Your gut is right. Listen to it!

As a part of our interview series called “Women Of The C-Suite” , we had the pleasure of interviewing Debra Fleenor, the Founder and President of Adapex, an adtech leader recognized by Deloitte as one of the fastest growing companies in North America and listed to the Inc 5000 in 2021. A serial entrepreneur and sought-after consultant, Fleenor is credited with two successful exits of 8-figure companies and more than 20 years driving disruptive innovation for tech startups. She’s an Admonsters and Folio: Top Women in Media honoree, and sought after thought leader on tech topics — from web 3.0 and the metaverse to artificial intelligence and the evolution of data privacy.

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?

My backstory can be characterized by a tension between my business life and my affinity for the arts. Early in my career, I spent time as an investment banker by day and art gallery worker and museum board volunteer in my off-time. I couldn’t decide which path I wanted to follow and felt split between business and creative worlds.

In 1987, these two worlds collided when I worked on setting up a multi-disciplinary arts center in Santa Monica. There was a live video art project that linked Century City, LA, Red Square in Moscow, and a square in Paris.

Within 24 hours, there were people and families gathered in Red Square and Century City meeting up through the project. All my traditional boundaries melted and I saw the future of a connected world. Keep in mind this was 3 years before the public had access to the internet, and many years before we ever thought about Zoom. The artists had shown us a world where digital connections broke down geopolitical boundaries. I saw a world in which creativity could bring disruption to invent a new business future, and a more connected future for people all around the world. I began thinking of business opportunities born from creativity & connectedness, and looking at the world with new glasses.

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

Our company has had a remote work structure since our founding. It was important to me to bake this structure into our company culture in order to foster work-life balance. In particular, we wanted to create an environment where working parents could thrive. This was important to me because of my own personal experiences as a working mom and my unwavering commitment to my family.

We got a lot of grief for our remote work structure — until COVID 19. We’re now in an environment where people are reconsidering their relationship to work spaces and to work life balance more generally.

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?

This one dates back to my first start-up, xoom.com. Xoom was a community site for developers to share and download gifs, jpegs, etc. It was in the early days of the internet, and we took off with a small investment, lots of enthusiasm, and a loose plan. As we were approaching the finish line to exit options, the cash began running out. We didn’t have the money to pay our employees. So, we started selling gadgets to our techy audience: CD holders, t-shirts, whatever we could get our hands on. Sales were slow until we made the desperate move to sell Beanie Babies. Believe it or not, our tech audience had a huge appetite for Beanie Babies. And those Babies took us right across the finish line to exit. From this I learned, plan, plan, plan, and always have a plan B. In this case, “BB.”

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?

All along the way, my father has been my leading mentor. As an entrepreneur himself, he taught me so many important lessons about sacrifice, the need for innovation & flexibility, perseverance and unrelenting determination. He taught me to put vision first, foster the team, and create an environment where everyone is working toward not just company goals but personal goals as well. He was my constant cheerleader and role model. I didn’t even know, feel or consider gender In/equality because my father put the same demands on me as my brother. He believed in me.

When I was honored by AdMonsters and Folio as a “Leading Woman in Media,” I was surprised when the women were asked, who do you have to thank? 30% said their elementary school teachers and 70% said their fathers. It struck me that there was a direct correlation between fathers who believe in their daughters and their daughters who achieve success. Shout out to all elementary school teachers and fathers. Believe in your girls. You’re the gas to their future acceleration.

As you know, the United States is 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?

As a female executive, and even more so in the tech industry where women are woefully underrepresented, I understand firsthand why it’s important to have a diverse team.

I was the first female Google Channel Partner, and for a long time I was the only woman to hold that distinction. It was not the first time I was the only woman in the room, but I have strived within Adapex and in my community associations to make sure this happens less and less. Being the only woman in the room is still striking to me, and it’s a reminder of my responsibility to represent women in technology, and to advocate for other marginalized groups.

It’s important that diverse voices are represented in the C-suite, and throughout the company, for the equity implications: a deep and personal understanding of the experiences and challenges of diverse groups brings in different perspectives. These perspectives stimulate creativity, and not only does this bring better solutions, it also strengthens opportunity for everyone.

A diverse executive team is important for innovation. Creating a space where different perspectives, experiences and environmental histories can work together to solve problems is an incredible strength. It’s not enough to simply have diverse teams, though. Empowering the individuals on the teams and creating a collaborative environment is crucial.

I’m really proud of our teams at Adapex. We’re 55% female and virtually all of our teams are gender-balanced. We’re also a remote-first company, and have been since our founding, in order to give working moms and dads an opportunity to grow their careers and still enjoy work-life balance.

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.

The first thing that business leaders need to do is to simply acknowledge that our current social structure is not equitable. The second step is to decide that we care to do something about that. The final step is to create an action plan and then hold people accountable to realizing progress.

I highly recommend the book “The Conversation” by Robert Livingston. He lays out a roadmap for how to have the conversations in workplaces without judgement and toward a shared progressive interest. One of the stories that he shares in the book that struck me is the case study of Massachusetts Port Authority. Thanks to visionary leadership, MassPort sought to level the playing field for the individuals that benefited from development in a very sought-after and profitable piece of land. Ultimately, they baked diversity requirements into development bids. It forced the traditional developers to seek out more diverse labor in order to bring projects to fruition. This is a great case study for how to extend opportunities beyond the groups that typically benefit from them.

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?

I’ll preface that it really depends on the company size in terms of what’s expected of a company leader; however, there are two things that most executives are tasked with: empowering employees and creating culture.

Executives need to empower employees by encouraging them to pursue their strengths and build an atmosphere that they want to stick with. Employees want to see an organization invest in their personal and professional growth and development, and executives must create that precedent and priority.

Company leaders must also create a culture of inclusion to help employees realize their importance and potential. Fostering a connection to an employee’s personal impact motivates them to do good work. Employee plays a critical role in the success of a firm, and they deserve to feel good about their contributions so that they feel more inspired, empowered and engaged. All of this leads to the success of an organization. And, importantly, it makes for a pleasant workplace for all.

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

CEOs don’t need to do it all. In fact, they should NOT do it all. We all have our strengths, and our weaknesses. Delegation is critical. Focus on your strengths, and delegate your weaknesses. As Peter Drucker said, “do what you do best, and outsource the rest.” When we live and work in this zone, we empower ourselves, and we empower our employees.

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

Women face innumerable challenges, and we can see this reflected in the data on fundraising — men are far more likely to raise investment capital — and in the gender pay gap — women are paid less for the same work. Women are also far more likely to face sexual harassment in the workplace. People talk about these issues, and there are smart people advocating for progress and better representation and treatment of women in business, but we still have a long way to go.

While we certainly need to advocate for equality outside our gender, as important, we need to work together to empower women to find their voices that advocate for equality. To all the women out there: look inside to know your inner strengths and share them out loud with the world. Don’t fall for your inner imposter syndrome; know you have value to give to the world. Know it, embrace it, and share it with all!

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

How much I love what I do. Previously in my career, I had a short attention span, and bored with jobs after a couple years. I founded Adapex nearly 10 years ago, and I still find challenge and reward every day. In the world of ad tech, change is the only constant. The industry boundaries are in constant shift, and we have to shift and create with them in order to survive and to thrive. From header bidding, to programmatic in app and CTV, to the future challenges around privacy and data, we are in a constant learning curve that keeps me on my toes, and still fully in love with what I do, even so many years later.

Is everyone 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 leadership describes a host of acquirable skills, which means that anyone can be a leader. Being an executive means adding some intention to leadership. An executive must be able to choose the right team, and then foster that team to follow the team vision and mission. They need to be able to influence toward long-term goals, and be pragmatic about relationships and tactics to achieve goals and empower people.

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

1. Go with your gut. Trust your intuition. Our mind puts out a lot of noise, but our guts lead us in the right direction. Our gut holds years of accumulated experiences and wisdom. Trust in it. This is particularly important for women as we tend to have less confidence in ourselves than men. Don’t give into the imposter syndrome. Your gut is right. Listen to it!
2. Don’t sweat decisions — especially reversible decisions. Every day you’re making decisions about things you know little about. But you have to make them, all the same. Don’t stop the train to deliberate too long over decisions. Just make the decision and keep moving. And if it turns out to be a mistake, embrace it for what it is: life lessons that are learned the hard way. Failure is feedback. The biggest mistake of all is not doing anything, so instead, keep the decisions flowing.
3. Pivot:. Above said, when you make the wrong decision be prepared to act on the lesson. Always be prepared to pivot. No company moves in a straight line, you will need to adjust, adapt, and even change directions along the way.
4. Find Mentors. You needn’t feel lonely at the top. Find mentors, colleagues, friends that you can bounce ideas around with. I have different people that I go to for different issues/topics.
5. Keep curious. Keep learning. The only constant is change. If you’re not learning, you’re not growing.

I work in the beauty tech industry, so I am very interested to hear your philosophy or perspective about beauty. In your role as a powerful woman and leader, how much of an emphasis do you place on your appearance? Do you see beauty as something that is superficial, or is it something that has inherent value for a leader in a public context? Can you explain what you mean?

At the risk of sounding cliche, I truly believe that beauty comes from inside and true beauty is not confined to physical appearance. As an executive, you have to sell a vision and there’s an aesthetic quality to that. A good vision has some inherent beauty and an executive is often tasked with being the face of it. What’s important is how we take care of ourselves and encapsulate our vision and values in our public appearance. We need to present a whole, clean, put-together image that conveys our values.

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.

I believe in the democratizing effect of the internet, and I believe we need to use it more to bring education to people who don’t have access to good schools. And especially to girls who are not allowed to seek an education. I am forever inspired by Sugata’s Mitra’s “ hole in the wall project” that showed us how children can teach themselves and each other with the help of tech. We need to expand these “holes in the wall,” to as many corners of the earth as possible. It’s not just good for the children, it’s good for society as a whole to have as many brains as possible to work on the huge issues we face today, such as the survival of the planet. This applies even closer to home as well, which is why I am also inspired by “Girls that code.”

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.

I love to meet young female activists in the technology sector. Any young women that might be reading this that have an idea or a vision, feel free to reach out.

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