Top Corporate Executive Naomi Wheeless is Empowering Black Women in the Boardroom and Beyond
Career Leadership Women

Top Corporate Executive Naomi Wheeless is Empowering Black Women in the Boardroom and Beyond

Naomi Wheeless
(Courtesy of Naomi Wheeless)

It is remarkable to witness women of color break barriers with their rise to positions of influence, affluence, and impact. Whether in business, corporate, political, educational, sports, the arts, or entertainment arenas, one thing is for sure, our presence is far too powerful to be ignored. Naomi Wheeless is no exception.

While in college, her career began by working in a call center in Columbus, Ohio. Through a succession of rapid promotions, Wheeless ended up managing managers before graduation. Within a few years, she acquired an arsenal of skills in developmental leadership, organizational strategy, and customer relations. The evolution of her career spawned across different industries, where she worked from Bank of America to ServiceMaster, the parent company of companies that included Terminix Pest Control, TruGreen Lawncare, and Merry Maids. At the time, she was managing several hundred employees.

Wheeless continued flourishing in her career at Capital One serving as SVP of Operations, leading one of its customer operations divisions. About four years ago, she was tapped by Square and moved to St. Louis to assume her present role as Global Head of Customer Success. Today, she leads over 1,600 globally. Given her myriad responsibilities, in 2020 she was appointed to the board of directors for Eventbrite.

Naomi’s proven track record creating world-class customer experiences and improving operations for thriving global businesses make her a fantastic addition to our board. We’re thrilled to welcome a leader of her caliber and expertise. –Julia Hartz, co-founder and CEO of Eventbrite.

Through her career trajectory, she has “always been open to relocat[ing] as it has made all the difference in helping me rapidly reach where I am. I was confident enough in myself to not be afraid to leave a company after several years to gain a new experience elsewhere.” In a candid interview, we caught up with Wheeless to talk about the experiences of Black women in leadership and executive positions and how we should show up best in the boardroom and beyond.

Naomi shares three qualities that African American women leaders, executives, and entrepreneurs should possess.


It’s essential to fully own the space you are in and always walk with your head held high. Be grateful for how far you have come remembering the trail of ancestors that led you to the present place you occupy.


Play chess, not checkers by becoming a visionary and mastering a strategic mindset with the ability to “see” many moves ahead whether personally or professionally.


If you desire something, whatever it may be, find creative ways to make it happen. Learn how to build strong cases when making an argument by developing your influencing skills. Figure out how to overcome imposter syndrome if that’s something you struggle with. Find creative ways to create connections with people who can positively impact your life. Insist that everything you do really counts and is highly impactful. Don’t give up the first few times you are told “no,” it simply means you haven’t found the right way to ask. Finally, if you’re going to make a move, then make a MOVE!

In terms of representation across industries especially within executive arenas, the ratio of African Americans varies. Typically, Wheeless is the youngest, one of few women, and nearly always the only Black in the room. According to her professional experiences, the number of women has grown but male counterparts still far outnumber in representation.

People of color still seem to be incredibly underrepresented at this level, in comparison to White executives. -Naomi Wheeless

Since our culture is generally underrepresented, it’s important to stand out visually. According to Wheeless, she has never served on a board that included another Black person. She’s especially proud of the work that Eventbrite is doing to bring more diversity to its board and other executive positions. She also shows up highly prepared, fully present, and engaged in conversations creating a climate that encourages company leaders to think differently or consider a unique perspective. For her, it’s all about bringing a mindset of digital transformation and customer experience, which are often unique qualities found with traditional board members.

Wheeless offers five practical strategies on showing up confidently for maximum impact in the boardroom or whatever table you find yourself seated at.

  1. Become comfortable with being uncomfortable. Force yourself into situations where you are going to be nervous and unsure of yourself on a regular basis.
  2. Practice, practice, practice! For instance, record yourself giving your presentation. Utilize trusted friends, and mentors as your practicing audience and incorporate their applicable feedback. Remember you can practice your confidence in “safe” places outside of your job such as volunteer opportunities within your community, your church, or your family.
  3. Be prepared and over-deliver! Do the necessary research you need to do, and then some more. Preparation is never a wasted opportunity. If you are not as prepared, this will only exacerbate your nervousness which adversely impacts your confidence.
  4. Display competence in your area(s) of expertise, operating in a spirit of excellence, delivering the highest value. This positions you to be irresistible, unforgettable, and a sought-after asset.
  5. Identify your spiritual grounding and take time to center yourself regularly. This ensures that you are continually operating from a place of calm, collection, and confidence.

Although a corporate heavyweight, Wheeless also has an entrepreneurial edge. She is multidimensional in transforming from a Black woman in the boardroom to boss! She shows up through her personal brand by empowering in life skills, leadership development, and as an inspirational and motivational speaker having been noted for her striking humor, sheer sarcasm, and quick wit. Her passion is evident by leading by example and pouring into others—elevating and upgrading their career profession, business, and life.