I think keeping them as Bitcoins until we need them to be converted is the best bet. Why? Because day trading loses money and trying to guess the best "out" is a waste of time. Overall Bitcoin goes up so leaving it until the last minute to sell is the safest option, it's possible that you get unlucky and the price drops at that time but that is the nature of the market.

TL:DR, Don't day trade, don't guess the market, just keep them until you need fiat.

EDIT: Also by doing this Ken does not have to worry about the wrath of the shareholders if he gets them into fiat at a bad time, because the money was needed and that would not change. If instead Ken starts guessing the market and fails, then everyone is going to be angry he lost money.

If Ken's algorithm for selling the Bitcoin is to wait until its needed, there is no room for error, because shit happens and you move on. If Ken's algorithm is sell high, I promise you everything will go totally wrong.
I used to day trade, but stopped because its stupid hard. I left that game with a small "not worth my time and hassle" profit and have never looked back.