As an update, I'm now at 318.5 -- down 14.5 since January. Most of that has been the last couple of months. Getting a personal trainer has been great, not only am I learning what I should be focusing my energy on in the gym, but it also holds me accountable to actually work out on a regular basis... eating better too.
It took a few weeks to even see a change after starting to work out, but noticed my clothings starting to feel a bit looser -- finally the scale caught up with what I've been doing.
With the weather getting a lot nicer, I'm planning on getting outside more bike riding, long walks, etc, on top of just hitting the gym.