No one could have predicted what would be in store when Charlie Boss, Bristol City Football Club’s new CEO, stepped into the role in late February. But in the couple of months since he’s taken the helm of the West Country team, he’s overseen a head coach change – parting ways with Gerhard Struber and bringing in former England manager Roy Hodgson as interim head coach – navigated a challenging Championship season, and faced vocal pressure from fans.

Clearly, in football, as in businesses more broadly, the big decisions don’t wait for you to settle in. In the latest episode of Inside the Workroom, as part of Employment Hero’s partnership with the club, UK Managing Director Kevin Fitzgerald delved further into what that journey has been like for Charlie, who brings a rare perspective to the role.

Charlie is no stranger to the world of sport. Before Bristol City FC, he spent nearly a decade at Disney, ran major racing events at the Jockey Club including Cheltenham Festival and the Grand National, and was part of the team at Southampton FC that navigated relegation and then won promotion back to the Premier League through the playoffs in 2024. He knows what it feels like when a club gets it right – and what it costs when it doesn’t.

His three-season target for Bristol City is unambiguous: the Premier League. But what stands out in this conversation isn’t the ambition itself – it’s how clearly the club’s CEO understands what has to happen before they get there.

Watch or listen to the full conversation below. Subcribe to Inside the Workroom wherever you get your podcasts.