This is what I think. I guess it’s a new football time we are in. Traditionally, I would have thought those achievements are seen as ‘during manager x’s time’, as opposed to during the CEO, kitman, physio or chief accountant’s time. Like, he’s a Chief Executive Officer. Ajax came across a golden generation of young talent and did well. Fair play. Not sure how that makes VDS so in demand now.
Ajax didn't just "come across" their golden generation. Ajax hadn't developed a single world class talent (outside of European talents brought to the club at 14-16: Vertonghen, Alderweireld, Eriksen) since Van der Vaart + Sneijder in 2000-2003. In 2001 the KNVB instituted LVG's redesign/overhaul of the Dutch (youth) football pyramid and development ideas/fundamentals/"manual", known as (not kidding) "the masterplan". this was implemented nationwide and (imo) directly caused the completely drying out pool of world class talent, the last being those two Ajax midfielders + Robben at Groningen and RVP at Feyenoord - all around the same exact time. Instead we started producing boring, competent "system players" like Klaassen, Van Ginkel, etc. At Ajax, these ideas were further pushed through by Van Gaal in his role as Technical director in the years following the masterplan (2004), though fortunately he left again fairly soon due to conflict.
Ajax produced completely mediocre talent for a full decade. In 09/10 Martin Jol's Ajax got humiliated in the CL by Real Madrid in a way that reflected none of the club's ideals nor any other element to even vaguely compete on the pitch with the Madrid's of this world. This inspired Cruijff to return to the club with what was coined the "velvet revolution", overthrowing the roundabout of management types that had been taking turns as the club's management the past decade and instead training and instating football people in those positions at the club. Van der Sar fit the profile perfectly and so he was approached and guided through his masters (at Cruijff's sport university) and then guided in his trajectory of learning the ropes at the club before finally taking on this position a good 5 years or so later.
Cruijff also overthrew the Ajax academy and the ideas of Van Gaal and Jan Olde-Riekerink through his confident and "vessel" Wim Jonk, who completely changed the whole paradigm of what youth football entailed at Ajax with ideas that were subsequently taken over by the Dutch FA nationally as well (like the "twin games" idea, but also the training on different surfaces with different size balls, rotation of trainers through the teams during a season, etc.). He, and with him Cruijff, left Ajax in 2015 following a dispute with (his best friend) Bergkamp (who two years later also forced the exit of our greatest coach since Van Gaal, Peter Bosz).
So it wasn't chance: Van der Sar was instated in/by the same process that overhauled the academy, leading to the talent that came through in recent years and also that which is about to come through again in the next 2/3 years (the 2002/2003 generation)
Who was their CEO in 1995? I mean, rightfully, to me anyway, LVG who managed the football team got plaudits and suitors after winning the CL. Nobody cared about the CEO.
Not the CEO (though this was before our listing so maybe it comes down to the same thing at the time), but funnily enough the Chairman at the time of our CL win in 1995 was Michael van Praag, son of Jaap van Praag who was the Chairman of Ajax from 1964 to 1978, the period of our three previous European Cup wins.
Also Van Gaal was a tremendous coach in the 90s and is a legend of the club. His success with youth however, as described earlier, went to his head. In my opinion, the success of that team can again be traced back to Johan Cruijff, who was manager (and Sporting Director) at Ajax from 1985-88, in which he also was very hands on in forming the academy to his vision, for example instating Jany van der Veen, the scout who discovered Cruijff himself, as the head of recruitment of the academy ( / as head of Cruijff's own recruitment "company" (as well)), who personally in this period recruited to the academy players like Davids, the De Boers, Kluivert, and Seedorf, a big core of that 95 team, as well as players like Witschge, Menzo, Winters.
Cruijff also personally tutored Bergkamp in a very hands on way btw, but that's a different thing. anyway I'm getting sidetracked. My point is just that in my eyes it's very far from coincidence that these success stories at Ajax and Barcelona seem to follow so closely from Cruijff's times at these clubs about a decade earlier.
About whether this makes Van der Sar a brilliant CEO? Not at all. He seems competent though, so far, though it's easy to appear that way when everything on the pitch is going so well. The criseses in his time at the club haven't been handled too well, particularly for me the Bergkamp - Jonk and Bergkamp - Bosz disputes, in which both times he chose Bergkamp's side (directly opposing Overmars who backed Bosz). This was resolved with Bergkamp (and his buddy Spijkerman + friend Keizer) a couple months later in a moved that consolidated more of the club's power with Overmars (and his new man Ten Hag).