From Radio City Phone Lines to MSG President: Meet Josephine Vaccarello

Some career paths are straight lines. Josephine Vaccarello’s was a staircase, and she climbed every single step. She started at Radio City Music Hall in 1998 as an administrative assistant, barely a month out of college, and this September she was named president of Madison Square Garden Entertainment. Billboard just crowned her Touring Executive of the Year, and the year she had makes the case better than any press release could.

Her 2026 was the kind of run venue executives dream about. The Garden hosted 57 shows this summer, its biggest season ever, up from 36 the year before. Harry Styles followed his 2022 Garden stretch with a 30-night residency. The Knicks won the NBA title. And Sphere, where she helped shape residencies like Billy Joel’s 10-year run and the Backstreet Boys’engagement, has now grossed $1.2 billion across 306 concerts since opening in September 2023. Colleagues describe her as unflappable in a crisis, a quality that matters when a live show can change direction in seconds.

What makes the story land for concert fans is that it’s the behind-the-scenes piece you never think about while screaming the lyrics. Every sold-out residency, every surprise comedy arena tour, every podcast that suddenly needs a bigger room runs through people who spent years learning how venues actually work. Vaccarello is one of them, and she started by picking up the phone. What’s the first job you ever had, and could you see it turning into this?