Josephine Vaccarello’s 28-Year Career: From Admin to President at MSG Entertainment

Josephine “Jojo” Vaccarello never planned to spend her entire career at one company. She just never wanted to leave.

Vaccarello, now President of MSG Entertainment, started at the company right after college in 1998 as an administrative assistant at Radio City Music Hall. Six months later, Madison Square Garden bought Radio City, and Vaccarello moved over with the team. That was the start of her 28-year journey through almost every part of the company’s live division, which led to her being named to VenuesNow’s All-Stars list and featured on the cover of Pollstar this year.

“I fell in love with it instantaneously,” Vaccarello says about her first year. “It’s part of your blood if you work in this industry, in my opinion. It’s just part of who you are.” She didn’t realize back then that she would still be there nearly thirty years later. But she says she loves the job just as much now as she did in her first year. And the numbers reflect that passion. According to Pollstar Boxoffice Reports, the Sphere in Las Vegas, NV, ranks #1 in the 2026 Q3 top 200 arenas ranked by gross, with $315,278,565 made across 1,551,086 tickets sold, while New York City’s MSG ranks #2, grossing $224,959,543 with 1,428,912 tickets sold. As for theatres, the iconic Radio City Music Hall tops the list of 200, grossing $192,582,949 across 1,457,809 tickets sold, while the Chicago Theatre and the Beacon Theatre both rank in the top 20.

Vaccarello attributes some of that success to her curiosity, a constant in her career. “I am inquisitive. I want to know how to do everything,” she excitedly states. As an administrative assistant, she moved up in the live division by asking questions like, “How do you do that?” and volunteering whenever she saw a need. She says she still works that way today, even as she oversees bookings across MSG’s venues. Vaccarello is always looking for ways the company can improve, try new things, and make the fan experience better.

One of the earliest tests of that instinct came when Vaccarello pushed to book a young Dane Cook, then still on the way up, for a run of arena shows, which was his first-ever at Madison Square Garden in 2006 and became the HBO Special, Vicious Circle. Putting a comedian in an arena setting was almost unheard of at the time, but the bet paid off across three or four sold-out nights. “The team here let me take that shot, and it was very successful,” she says. “That was a big jumping-off point for me.”

That bold approach has shaped some of MSG’s most memorable bookings. Billy Joel’s ten-year residency at the Garden, which Vaccarello helped lead, felt more like a big family reunion than just another tour stop. She describes it as “hugs and high-fives in the hallway.” She used the same approach with Harry Styles, whose 15-night “Harry’s House” residency became one of the year’s most talked-about concert runs and later grew to the 2026 30-show behemoth a part of his “Together, Together” tour. “The energy within the arena during Harry’s show is truly palpable,” Vaccarello exclaims. “If I could take that and bottle it up and sell it, everyone would be happily euphoric.”

Vaccarello has used the same intuitions outside of music. Jerry Seinfeld’s residency at the Beacon Theatre, which is just a few blocks from his Upper West Side home, and a 22-night sold-out run of “Les Misérables” at Radio City last summer both show her belief that comedy and theater should get the same special treatment as big concert residencies. “It’s just the right fit,” she says about Seinfeld. “Again, it’s that home connection.”

Technology has played a big role during her time at MSG. The recent Sphere Immersive Sound installation at Radio City Music Hall added more than 7,000 speakers to the century-old theater in about six weeks. This project meant rethinking a building known for its acoustics while keeping its iconic feel. The result is beam-forming technology that makes every seat “the best seat in the house,” a sound Vaccarello compares to someone singing to you in your own living room. She says artists are usually a bit cautious the first time they hear it, but once they do, their hesitation turns into excitement.

Her and her team’s drive to innovate now includes Sphere itself, a venue that Vaccarello says uses a completely different approach. Its lighting, sound, and video are built into the building instead of being brought in with each tour, and the technology was developed with the Sphere Studios team. “We’re still scratching the surface of what is possible in that space,” she says. She adds that the company’s plans to bring Sphere to new cities around the world will help shape the company’s next five to ten years.

After nearly thirty years, Vaccarello sees mentorship as a key part of her job. “It is my job to teach the same way that someone taught me or gave me the opportunity to do something,” she says. The seasoned exec credits the dedication of MSG’s bookings and venue teams, a group she says works nights, weekends, and holidays because, for them too, “this business is in their blood.”

Asked what’s still on her wish list after 28 years, Vaccarello doesn’t hesitate to point forward rather than back. Between Sphere’s global expansion and the momentum from Les Mis’s Radio City run, she suspects the next chapter of MSG’s live business is only just taking shape.

“As we look at expanding and building more Spheres around the globe, that’s an interesting part of what the next five to ten years will look like for us,” she says. “And who knows what comes next, but it is exciting to work in these iconic buildings, especially on the legacy side of the business.”

_Originally reported by [Pollstar](https://news.pollstar.com/2026/09/21/in-her-blood-josephine-vaccarellos-28-years-building-msgs-biggest-moments/)._