Some careers are built on opportunity.

Others are built on consistency.

Skip Dillard’s career has been built on both.

For more than 30 years, Dillard has quietly become one of the most respected programmers, executives, and brand builders in Urban radio. While many industry leaders have enjoyed successful runs at one or two stations, Dillard’s influence stretches across multiple major markets and some of the most recognizable call letters in the business. From New Orleans to Washington, Detroit to Buffalo, and ultimately New York City, his fingerprints can be found on stations that helped shape the sound of Urban radio for generations.

Born in Queens and raised in Greensboro, North Carolina, Dillard’s broadcasting journey began long before he ever occupied a corner office or executive title. While attending Hampton University, he gained experience at WHOV-FM and also worked at WOWI-FM in nearby Norfolk, Virginia. Those early opportunities provided the foundation for a career that would eventually take him to some of the nation’s largest markets.

After graduation, Dillard worked at WQMG and WJMH in Greensboro before heading to New Orleans, where he joined the legendary WYLD-FM. It was there that he began making a name for himself as both an on-air talent and programmer, eventually rising to Program Director. For many broadcasters, becoming Program Director at a major Urban station would be the pinnacle of a career.

For Skip Dillard, it was only the beginning.

Over the years, his career path would include programming and leadership roles at some of Urban radio’s most important stations. His resume includes stops at stations such as WYLD-FM New Orleans, WBLK Buffalo, WMXD Detroit, WPGC Washington, and WOWI Norfolk. Each station represented a different challenge. Each market demanded a different approach. Each stop added another layer to the leadership style that would eventually make him one of the industry’s most respected executives.

One of the things that separates Dillard from many programmers is his ability to balance data with instinct.

Great programmers understand the numbers.

Elite programmers understand the people behind the numbers.

Throughout his career, Dillard developed a reputation for understanding audience behavior while never losing sight of community connection. He recognized early that Urban radio wasn’t simply about playing music. It was about culture. It was about identity. It was about serving listeners who often viewed their favorite station as part of the fabric of everyday life.

That philosophy followed him everywhere.

In 2003, Dillard stepped away from radio programming for a brief period to become Managing Editor for Top 40 and Urban formats at Billboard’s Airplay Monitor. The move provided him with a unique opportunity to study the industry from a national perspective. Rather than focusing on one station or one market, he was now examining trends affecting radio across America. The experience broadened his understanding of programming, music, audience behavior, and industry evolution.

When he returned to radio, he returned with an even larger vision.

That vision would eventually lead him to one of Urban radio’s most iconic brands.

WBLS.

There are successful stations, and then there are legendary stations.

WBLS falls into the latter category.

For decades, WBLS has served as one of the most influential Urban brands in America. Artists have built careers through its speakers. Communities have rallied around its airwaves. Generations of listeners have trusted its personalities and programming.

When Dillard joined WBLS and sister station WLIB, he wasn’t simply programming radio stations.

He was helping protect a legacy.

During his 12-year run as Vice President of Programming and Operations Manager for WBLS and WLIB, Dillard helped guide the stations through one of the most disruptive eras in broadcasting history. Streaming services exploded. Social media changed music discovery. Digital competition intensified. Audience measurement systems evolved.

Many heritage brands struggled to navigate those changes.

WBLS continued to thrive.

In fact, under Dillard’s leadership, the station achieved some of the strongest ratings performances in its storied history while successfully transitioning through the industry’s move to electronic audience measurement. That’s no small accomplishment when you’re responsible for one of the most historic brands in Urban radio.

But ratings alone don’t explain Skip Dillard’s influence.

His impact reaches far beyond the studio.

Throughout his career, Dillard has been heavily involved in community service, mentorship, diversity initiatives, and nonprofit leadership. His work has earned recognition from Congress, Radio Ink, the Living Legends Foundation, New York City, New York State, and numerous civic organizations. Those honors weren’t awarded because of ratings books.

They were awarded because of impact.

The industry often talks about servant leadership.

Skip Dillard has spent decades demonstrating it.

Whether serving on industry boards, supporting diversity initiatives through the FCC’s Communications Equity and Diversity Council, or helping develop future broadcasters, Dillard has consistently invested in the next generation. That commitment has helped solidify his standing as one of Urban radio’s most respected voices.

Then came another challenge.

Building a brand from the ground up in New York City.

In late 2021, Audacy selected Dillard to become Brand Manager of the newly launched 94.7 The Block. The decision made perfect sense. Few executives possess a deeper understanding of Urban radio, New York culture, and audience engagement than Skip Dillard. Audacy wasn’t simply hiring a programmer.

They were hiring a builder.

Today, Dillard serves as Vice President and Brand Manager for 94.7 The Block and Audacy’s Rhythmic AC stations. The station has carved out a strong position in the nation’s largest market by embracing classic hip-hop, throwback culture, community involvement, and listener engagement. The formula sounds simple.

It isn’t.

Making radio feel authentic in 2026 remains one of broadcasting’s most difficult assignments.

Skip Dillard continues to make it look easy.

As someone who has spent more than three decades programming radio stations across America, I’ve learned that truly great programmers share a common trait. They leave every station better than they found it.

Skip Dillard has done that repeatedly.

Market after market.

Station after station.

Decade after decade.

His career has never been about chasing headlines. It has been about building brands, developing talent, serving communities, and protecting the integrity of Urban radio.

That is why Skip Dillard remains one of the format’s most respected leaders.

And that is why he is this week’s On The Dial Power Player.

Steve Mills, President and Publisher of On The Dial, said, “I’ve always believed the best programmers understand that radio is a people business first. Skip Dillard has spent his entire career proving that. Whether it was WYLD, WBLK, WMXD, WPGC, WBLS, WLIB, or now 94.7 The Block, his ability to connect brands with communities is exceptional. He is one of the finest Urban programmers of his generation, and his legacy is still being written.”

On The Dial’s Power Players, Past and Present recognizes the executives, programmers, personalities, managers, owners, and visionaries whose leadership continues to shape broadcasting while inspiring those who will follow.

On The Dial covers breaking radio industry news, including layoffs, programming changes, talent moves, and broadcast trends across the United States.