Ashley Henderson at Hilltop Coffee + Kitchen, Inglewood location (Shelby Stephens/L.A. Sentinel)

It’s been ten years in the making for entrepreneur Ashley Henderson. The Los Angeles native, Chief Creative Officer, and founder of League Twenty-Two, is building a marketing empire with star-studded clients like Nike, NBA, YouTube, and Estee Lauder.

As a millennial female owned agency, League Twenty-Two is engaging all areas of marketing to enhance Back representation in the media, specializing in event production and fabrication, creative strategy, and content curation. Through this, they provide an array of creative services that take their efforts to new heights and stand in a league of their own.

Before graduating from Howard University with a Public Relations degree, Henderson was a student athlete in high school. She was encouraged by family and friends to pursue a career in broadcast journalism because of her upbeat and bubbly personality. After selecting her major as just that, she quickly realized she was more comfortable working and executing projects behind the scenes. “I applied to all the schools and deciding on Howard University was the best decision I ever made. I was able to host events on campus for students and work the logistics.”

During her time in college, she interned with Interscope Records, WHUR Radio in D.C., and interned with Michael Eric Dyson. During these internships she dominated special events planning. After graduation, Henderson became a corporate executive at Estee Lauder as the Regional Events Manager at MAC Cosmetics, producing all west coast events for the global brand. “Being an employee of Estee Lauder and now having them as a client has been complete full-circle moment for me.”

Working side jobs while being employed full-time, Henderson knew she had to switch it up and start working for herself. League Twenty-Two launched in 2016, Henderson came on full-time in 2018, and now the agency serves clients in Los Angeles, Miami, and New York. Their mission is to connect brands with cultural audiences, with a focus on beauty, music, sports, retail, and philanthropy.

“Our first event was for charity at the Boys and Girls Club where we collaborated with NFL players Omar Bolden and Bobby Wagner to give back and make an impact in the community. Starting events and paying homage to my friends in the NFL, we have been able to execute football camps and secure sponsors. Our second event was with Girls with Gifts, who’s main goal is to inspire and empower young girls.” Henderson explains that philanthropy is a big influence in her marketing journey.

Henderson is the founder of League Twenty-Two and aims to build a marketing empire. (Shelby Stephens/L.A. Sentinel)

“As a small marketing agency, we can leverage our youth and way of thinking in the marketing space. When we secured Nike as a client, I cried. We’re three seasons in and we’ve made history by being the first and only agency to highlight HBCU students on a global level.” Henderson shares this has been one of the highlights of her career. Because the League Twenty-Two team is the target audience brands are trying to reach, they authentically bring cultural relevance and expertise to their clients.

In the midst of sharing the ups of her profession, Henderson also gives insight to the challenges of being a small, Black owned, and female oriented marketing agency. “We constantly have to prove we’re just as good or better than counter agencies. Securing big budgets and gaining our clients trust to handle such upscale projects, requires opportunities to grow the capital to hire and execute at such a high level.” As most agencies are male dominated, with little to no diversity or multi-cultural aspects, League Twenty-Two’s unique skills and out-of-the-box thinking set a new bar for what brands can do to market and connect with their customers.

League Twenty-Two is a growing commodity. When asked about her inspiration and what keeps her motivated, the proud member of Alpha Chapter, Delta Sigma Theta Sorority shared, “I take the ‘no hands off’ approach. I attribute my work ethic to Delta. I am motivated. No one can outwork me.” She explains practicing gratitude and remembering where she started keeps her going. “Hard work, consistency, and discipline pays off. To young women, don’t compromise your values and focus on balance. That’s what I’m working on now.”

In five years, Ashley Henderson strives to establish another League Twenty-Two office in New York, support a staff of 25 people, and expand the agencies opportunities for long-term partnerships. “The goal five years from now is for League Twenty-Two to lead the largest Black campaign and to continue to keep amplifying Black voices and Black stories.”