I thought he had. I know Bayern have used one for a long time now so I'm almost certain he would have there at a minimum.
- Juventus. Worked under legendary transfer guru, Luciano Moggi.
- Milan. Worked with one of the most domineering and invasive executives of all time in Silvio Berlusconi, who was very involved if not dominated transfer policy (and everything else).
- Chelsea. Worked under Roman Abramovich / Frank Amesen as a combo who were primarily responsible for transfer strategy, which included strange Russian player purchases (Yuri Zhirkov) and poor fits (Fernando Torres) with bad market returns.
- Real Madrid. Worked under domineering Florentino Perez, who likely bought Gareth Bale to set the transfer record at the time amongst other players and seemed to automatically fire managers every year or so.
- Bayern Munich. Worked under Uli Hoeneß who was a club legend, uber traditional, and was very active – to the extent that he pushed an assistant coach on Ancelotti in Sagnol that might have contributed to him “losing the dressing room”.
- Napoli. Worked under Aurelio De Laurentis who didn’t seem to lack ego and was heavily involved in club operations. Ancelotti’s lack of support for the De Laurentis imposed November bootcamp probably contributed more to his removal than his team’s performances.