I'd start by throwing a pile of money at Gruden. If that doesn't work I'd go after Lovie Smith and have him find an OC that can run an offense with what the Browns have to work with. Smith would be able to build on the defense that the Browns already have in place and has been a successful NFL HC.
Spend the draft making the D better with the high picks and look to sign a few key FA's to fill out the other holes.
Bring back Dawson even if they have to overpay. I'd hate to lose games that they need to win because they are breaking in a new kicker. I'd like to see a deal that is light on bonus, but an even year to year pay for as long as he is able to be a successful NFL kicker. If he demands a bonus I'd look to guarantee the first few years and then make everything else more of a year to year deal.
Greatest Needs:
Pass rush DE/OLB or
near Haden level CB
at least one guard
S (could be Sheldon Brown for the right price)
TE that can block and catch to replace Watson although Cameron will be the starter
FB (Boren please - good blocker, good catcher, good at ST's)