Dempster spent six years at Easter Road before her departure in late 2020. She previously spent time in charge at Motherwell after moving up from the general manager position and is now CEO at League One Queen’s Park.
When asked on the podcast for her experiences of being one of the few female chief executives in the SPFL, Dempster responded with the shocking story.
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"My welcome to the first game in the boardroom was to have my backside slapped by somebody, really hard,” he said.
"It was actually on the way to the boardroom. It was a staff member, it wasn't a director or anything like that.
"I was so shocked, I hardly did anything, to be honest. Afterwards I went back and said to him, 'one time only,' type thing.
"I took it for what it was at the time. I don’t want to make too big a thing of that because worst things have happened, let’s put it that way, though not in football.
"Being the only woman in the game is something people would always focus on that in the past. But visibility around the game is just wonderful, participation in the game is wonderful now, so I don't really think about it. I've always worked in male-dominated environments."
On the podcast, Dempster also expressed regret around the circumstances leading to Neil Lennon’s departure as Hibs boss in January 2019.
The ex-Celtic manager, who led Hibs to the Scottish Championship crown in his first season and a club record points tally in his second, was suspended by the club following an alleged bust-up at the Hibs Training Centre before officially leaving alongside assistant Garry Parker four days later.
"I genuinely regret the way Neil Lennon left Hibs,” she said. It was probably at a point where it had to happen, for him and for us, I just regret the way that it happened. So if I had to do that over again in a different way then I probably would.”