Your company can do it, with or without a lawyer.
If you file duly during OPT and the H1B cap is available or not subject to cap, yes, you can wait legally, but can't work after OPT expires.
If denied before OPT expires, you can file again. If denied after OPT expires, you are out-of-status.
If you file duly during OPT and the H1B cap is available or not subject to cap, yes, you can wait legally, but can't work after OPT expires.
If denied before OPT expires, you can file again. If denied after OPT expires, you are out-of-status.