I like the idea but there are several factors that make this an un-enjoyable experience in my eyes:
1) It is too easy to get to the top, with no incentives to save money and no fear of dying.
2) The CEO is too powerful when compared to the monsters you had to fight on the way up.
3) Your probability engine / calculator (whatever you want to call it) is wrong. On my 3rd play through, I chose the Barbarian Class, using the "Stab" attack against the CEO, I missed 41 out of 47 times before I rage quit. Your text reads that it will miss 35% of the time, either I should have spent my time better this evening putting on a lottery ticket with those odds, or your engine is wrong ...