Cindy Webster Reflects on Her Career in Radio
On April 2, 2020, when Cindy Webster received word by phone that she was being laid off from her job as marketing director at SportsRadio 94WIP, it was quite literally like a curveball coming out of left field.
But for Webster, a lifelong Philadelphia Phillies fan, this was no baseball game.
“It was surreal, like a punch in the gut,” recalled Webster, 54, who had worked for CBS Radio and then Entercom (which purchased the radio division in 2017) since 1992. That 28-year stint encompassed a diverse array of activities and accomplishments at top-rated Philadelphia stations: SportsRadio 94WIP, 98.1 WOGL and Talk Radio 1210 WPHT.
“Between sporting events, Wing Bowl and some amazing things related to the music industry, I even high-fived a Masters champion right after he won,” said Webster, reflecting on highlights among the thousands of events and once-in-a-lifetime experiences that defined her career.
Like so many whose lives have been upended by the global pandemic, Webster’s altered reality began on Friday, March 13 when massive shutdowns forced scores of the workforce into their homes. Webster quickly transitioned from her Philadelphia office to her home in a Montgomery County suburb. But the news that arrived a little more than two weeks later—that her position had been eliminated—was even more unexpected and dizzying, to put it mildly.
“I was one of the most tenured staff in the country that was let go,” said Webster, describing herself as the station historian of sorts, the “go-to” for information and resources. Bryan Cole, who was WIP’s promotion director and Webster’s “right-hand man,” also lost his job.
Webster attributed much of her career success to incredible teamwork among colleagues.
“Bryan and I were together in the trenches from 2008 until 2020,” she explained. “It’s been a really tough loss after three decades of my life devoted to the same company.” In fact, prior to her time at CBS Radio/Entercom, she worked for Delmarva Broadcasting for four years where she held marketing positions at 93.7FM, WSTW in Wilmington, Delaware.
So much of Webster’s professional life was about people, relationships, in-person events, and being in the mix of activity. To have that suddenly torn out from under her has been a bitter reality. Yet she knows that many others are experiencing similar losses.
Webster had dedicated her life to a job and a career she loved. It was a 24/7 passion that she poured her heart and soul into. It certainly wasn’t a 9 to 5 gig, nor one without stress or sacrifice. Her job often entailed nights, weekends, whatever it took to direct and complete each task, such as orchestrating marketing and public relations blitzes, accompanying talent onto the field before a game and much more.
“It was my life,” said Webster, one that fit her outgoing, people-oriented personality to a T, where she felt purpose and fulfillment.
“It wasn’t the traditional marketing director position,” continued Webster, adding that the job evolved over time. “I did everything from working with all the talent as well as coordinating and overseeing events, concerts, fundraisers, on-air contests.” She even became a recurring on-air contributor (as a fan) on Angelo Cataldi’s Morning Show. “People got a kick out of my fan insights,” said Webster who not only loves the Phillies, but is a fan of all Philadelphia sports teams. “Angelo is one of the most talented people,” said Webster of her longtime colleague and friend. “He has a knack for knowing how to bring in guests to diversify his show. One day, he might have a Tastykake delivery man on the air; the next day, a company CEO.”
Cindy Webster with the Phillie Phanatic
Webster looks back at many meaningful moments, including some history-making events like when the Phillies won the 2008 World Series. It was the same year her former boss tapped her to oversee marketing for WIP. At that time, she was still at WOGL and WPHT; WIP was added to her busy repertoire. It had been 28 years since the Phillies had reached such a height. Webster canceled a trip to Italy to stay home for the games. “That’s how much the team meant to me,” she said. And in the midst of the playoffs, to honor a friend, she completed the Susan G. Komen 3-Day, a 60-mile walk to raise funds for Susan G. Komen Race for the Cure and to promote awareness to fight breast cancer.
Webster recalled being fully immersed in the hometown magic; she not only worked on promotions for the playoffs, but she also attended as many games as possible—as a fan, including the night they clinched the series on the home field. She went to that game, against the Tampa Bay Rays, with her brother, Ricky Stover. It took place over two nights due to an extended rain delay on night one. After the win, she was in a celebratory tent alongside Phillies’ front office staff, alumni, broadcasters, media, special guests.
Webster remembers standing next to Greg Luzinski, a former player from the 1980 winning team. The recollection of that night still feels surreal to her. “I can’t explain how incredible it was,” said Webster who had watched her team win the series nearly three decades earlier. That time it was on television alongside her brother and parents. “I was 14 at the time,” said Webster. “After the game, everyone went outside and started banging pots and pans.”
The people Webster encountered over the years and the relationships that flourished are far too many to enumerate. She feels incredibly fortunate that she had the opportunity to get to know so many remarkable individuals. She developed relationships with beloved Philadelphia announcers, including the late Harry Kalas and Richie Ashburn. There’s also former Phillies manager Charlie Manuel—who coached the team to the 2008 World Series—and his wife, Missy.
“They have become dear friends, which is amazing since he gave me some of my best memories as a Phillies fan,” said Webster, who was raised in Erdenheim, Pennsylvania and had long envisioned a career in radio.
Webster graduated from the University of Delaware with a bachelor’s degree in communications. “I’ve always loved sports and music,” she said. “My dad loved music, and rock and roll.” That passion spilled over to his daughter who knew she wanted to do something behind the scenes. As a college student, she accepted an internship at Wilmington’s WSTW and immediately fell in love with the industry. A week after graduation in December 1988, Webster was hired as the station’s promotion assistant. She was later named assistant promotion director and then director.
Admittedly, working in the sports arena—clearly a field dominated by men—has had its share of challenges. “There’s a lot of ego involved,” said Webster. “It took me awhile to navigate and not to take things personally.” She would often find herself looking at things with a warm and fuzzy perspective. “I needed to be less emotional,” said Webster, who rose to the challenges, carving out her own unique niche.
Some of the most heartwarming rewards of Webster’s career came in the form of having the ability to make a difference in people’s lives. She cited one example of an email she received several years ago from a father whose young adult son was suffering from a brain tumor. The son was a huge Philadelphia Flyers fan. The team had made the playoffs and the father wondered whether the station might be able to obtain tickets for a game. Not only did Webster deliver on that request, she reached out to the Flyers to determine if they could do anything that might brighten this young man’s life. Her contact asked if he might want to ride the Zamboni in between periods.
The answer: a resounding yes.
“The father later contacted me,” remembered Webster. “Sadly, his son had passed away. He wanted me to know that being at that game was one of his most cherished last memories with his son.” That meant the world to Webster, who often tried to go above and beyond to make even the smallest of dreams come true.
On a more personal note, Webster added: “I always tried to be a good friend,” something that has come back around in unexpected ways. “People have been amazing. They’ve stuck with me and supported me during this time.” She’s even received cards in the mail offering words of understanding and encouragement.
Acknowledging that the world and the workplace have dramatically changed as a result of the pandemic, Webster is taking the time to figure out her next steps. “I’m lucky enough to have done something I love,” she said. “I want to find something that’s the right fit for me.”
