Pros
In honesty, the Booking IT department has a couple of things in its favor. The job is not demanding, most team leaders are reasonable (and you can put in for a transfer) and the relocation perks to Amsterdam are noteworthy. In other words: Booking.com is an excellent way to immigrate to Europe, and get a foothold in the job market here. For that, it gets the one star.
Cons
The lack of vision in general is easily attributable to the company being unchallenged on its existence for over a decade. In the absence of a vision, everybody is just maintaining the status quo, not coming up with new ideas and not doing anything to improve upon things. Because why would they? This applies to everything. Management is becoming less and less connected to what happens on the floor, and technical reasoning is virtually absent. While the people are generally reasonably skilled, the 80% expat staff composition means that nobody has a safety net to complain... and even if you do say no, some new guy will step up and (naively) say yes. Voilá, structurally ensured bad decision-making. The CIO is keen on repeating (and you can even see that dogmatism leak into the positive IT reviews here?) that Booking is "not a technology company." Considering that this is from the Chief Information Officer, it's not entirely unfair to conclude that it fails even at being even an Information Technology company -- it only has the offices, perks and explosive growth of one. Underneath the hood, it's looking a bit like a stock market adventure, or a perl hacker's playground, depending on job title. Some people are really caught up in this, and can't discern factoid from fact anymore. Tragicomically, the one thing Booking would benefit most from would be exactly that: being a technology company. Booking is troubled with problems on a daily basis that you wouldn't believe could exist in a space between 750 capable programmers, and still, it refuses to modernize what is, essentially, an engorged LAMP stack tracing back to its company beginnings. For anyone considering applying there, and for that matter for the cleverer heads who haven't jumped ship yet, I have to pose the question of whether you think that Booking is good for your career as an IT professional. Nobody else wants perl. Nobody else wants a shell cowboy. How long will the illusion last?