Ah right Football Man/Person/People got you.
VDS was obviously a player but Marotta is interesting as he wasn't though he has worked in football for a long time.
I'm interested in your opinion on how long a person has to work within football before they become a 'Football person''?
Marotta has a football CV which is as long as a man's arm having worked himself up to the top. In fact prior of joining Juventus he was Director of youths and GM at Varese, GM at Monza, Como, Ravenna, Venezia, Atalanta and Sampdoria.
Your question is very difficult to answer as it depends on many factors
A- It depends on the person in question. Some people are more analytical then others. Take Gaz and Evra for example whose pretty analytical and then compare him to lets say Rooney who tend to speak like a 5 year old
B- It depends on the upbringing they get. Some clubs like Ajax, Milan and Juventus are proud in developing people not players. In fact their success rate in terms of coaches, managers and football people tend to be higher then those at other clubs.
C- It depends on the person's experience. Many players tend to hop from one club to another. VDS for example had worked under LVG, Carlo Ancelotti, Lippi and Sir Alex picking secrets from some of the best directors in football. He played in 3 different countries and had experienced what it feels like being at a selling club who relies heavily on youths for financial survival, a top club who must win trophies and a club who fights to stay away from the relegation zone. You can't compare this wealth of experience with that of let's say Paul Scholes who never left greater manchester and had only worked with 1 manager (who made football look easy)
D- It depends on the club they will be working with. Varese is not Venezia, Venezia is not Atalanta, Atalanta is not Ajax, Ajax is not Juventus and Juventus is certainly not Manchester United. Sure Juventus might sound an equal/bigger club at this point in time from a football perspective. However when you consider the exposure, the money involved, the sponsorship deals that need to be made to keep the whole darn thing afloat, the brand name, the youth academy, the amount of fans etc then we're way bigger then Juventus. Juventus is a top Football club. We're a frigging juggernaut whose worth 3b-4b pounds. I struggle to think of any CEO with the skillset needed to manage all that alone.
Sir Alex used to speak about the importance of having the football side and the business side separate and independent. I think we've grown so much at this point to need to have 2 CEOs, one who takes care of the financial side and the other who take care of the football side. VDS on his own would probably fail. VDS and Woodward would probably do the trick.