How Ashley Henderson Pushes The Culture Forward—on Her Terms


Ashley Henderson has created a league of her own.

With her brainchild, League Twenty-Two, a culturally-empowered, millennial, boutique, experiential marketing agency, the Los Angeles native is pioneering the way for clients to achieve the near-impossible. The growing team of eight now serves clients nationwide.

Founded in 2016, the female-owned and -led agency exists to connect brands with cultural audiences.

As a proud HBCU alumna and proud member of Alpha Chapter, Delta Sigma Theta Sorority, Henderson reps Howard University and serves as the league’s founder and chief creative officer.

“Since Howard changed my life, I would like to make sure that I help and influence other HBCU students in the same way,” Henderson tOLD BLACK ENTERPRISE.

“We are intentional about hiring HBCU creatives, such as photographers, videographers, production assistants, and Black-owned catering companies, as we have been doing for many years,” she added.

Corporate beginnings

Before graduating from Howard University with a public relations degree, Henderson dominated in hosting and special events. She then served as regional events manager at MAC (Estee Lauder Companies) until she was inspired to champion the power of creativity and cultural strategy at her own agency.

At Estée Lauder, Henderson learned how to market products. Her emergence came when the beauty industry was booming, so she relocated from Los Angeles to New York to pursue the global beauty stage.

“I got a chance to work on large beauty events, like generation ipsy, beauty con, and I got a chance to work on Mac cosmetics, one of the most popular beauty brands at the time, as well as curate and activate different creative events the consumer would love,” she says.

“The experience I gained working with big corporate names inspired me to create my own agency that resembled me and created for individuals like me with the knowledge I gained from working with these larger corporations.”

 

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With her creative leadership, Henderson not only leverages her unique experiences of Black and Bison pride, she channels her skills as a former corporate executive in the beauty industry.

“I left Estee Lauder in 2018 to run my own company full-time. Everything I learned from Estee Lauder I took to my company and now Estee Lauder is one of my clients,” she saID.

She added, “If you take it down to numbers, Latinos are the number-one consumer in the makeup industry. Cultural strategy must be authentic. Black people have a trillion-dollar spending power, so if you think about it Black and Brown people are what make up most of the spending in retail and shopping.”

League Twenty-Two curates unforgettable experiences through strategic insight, experiential production, cultural reference, and engaging content for the likes of Nike x Lebron, Nike x YardRunners, Estee Lauder, META, YouTube, Beautycon, Jordan, and Diageo.

“As a small brand, when you want to engage with customers you need to identify who the target audience is,” Henderson observeD.

“Then if you have the tools to survey them, then ask their needs, their spending habits, and study the trends. Attaching your brand to an influencer in an organic way is a good way to push your brand forward. Even finding macro-influencers who are loyal to specific brands and can speak to their community in an authentic way is very important.”

 

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The number 22

The League Twenty-Two team is the actual target audience brands are trying to reach. Named after numbers symbolizing precision and balance, the agency brings a robust understanding of how to deeply connect with the millennial and Gen Z audience by emphasizing true cultural relevance and social awareness.

But it’s not as easy as it looks. Henderson experienced challenges from being overlooked by larger corporations, to scaling and capital raising challenges.

“As a result, we’re competing with larger non-diverse agencies that have been grandfathered in and that market to Black people but do not have any people of color on staff,” Henderson said about her challenges as a Black woman founder.

“That’s why they target us by using top athletes and brands to sell to us, yet we have no ownership, even more so, it’s important that we have equity and have a stake in this,” she addED.

(Courtesy of League Twenty-Two)

For year two of the Yardrunners campaign, where Nike celebrates HBCU culture through sport, Nike tapped agency League Twenty-Two to produce and execute the multi-platform campaign.

“I want to speak authentically to those individuals whose interests align with ours. The projects I am working on must push the culture forward, they must be multicultural, and they must have a purpose.”


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