50 to 100 ton USCG Upgrade - My next steps?

Hello all I am new to this forum. Not so new to the marine industry.

It all started as a young navy brat, following my dad from place to place in the US. First sailed in Groton, Connecticut just in view of general dynamics. Eventually ended up at Kaneohe Yacht Club in the junior program, before moving on to going on commercial fishing trips with my uncle out of Astoria all through high school during my breaks. This led to college sailing at UofO and Oregon State, with a two year stint of commercial fishing out of Astoria and a trip long lining in dutch harbor.

After graduating from college I started racing on big boats and lasers and doing other things like running sailing schools, clinics, and race management.

This last year I got my 50 ton Master with near coastal and sailing and towing endorsements and started http://www.coastguardcaptain.com/ and http://www.go-sail.org/. Then on December 1 started working at http://jtmarineinc.com/ as and exec project manager and potential tug captain.

Which leads me to the title of this post … My next steps …

I am looking for the quickest path to my 100 ton rating (for my delivery business), and also what steps I should take that would get me into the wheel house of jtmarine tugs (we have 6 of them and there is only one licensed tug captain).

Any comments greatly appreciated.