In the U.S., operations under FAR Part 135 are not quite the same thing as flying an airliner. It is true that all aircraft operating under Part-135 must be on a flight plan. But if a regular ol' FAA flight plan is not used for each flight, then the company must have "flight-following" procedures in place which include all of the information on an FAA flight plan, plus a method of notification of overdue aircraft. In other words, the FAA allows operators to flight-follow their own aircraft without the requirement to file individual FAA flight plans. (But this does not preclude the company from having pilots file FAA flight plans either.)
I think that some people must incorrectly interpret the FAA's requirement that all aircraft operating under FAR Part-135 must be on a flight plan to mean that there has to be takeoff-to-touchdown monitoring of every flight. Typically this does not exist. Typically, dispatchers *don't* sit at a screen monitoring the movement of every helicopter that's in the air like an air traffic controller. It's nice to fantasize that this happens, but usually it's not the case.
The FAA is pretty airplane-centric. Mandating that "135" flights be on a flight plan only means that someone will care if you don't arrive at the destination. And then if you don't arrive, it could be up to 30 minutes before anyone starts looking for you. In my career, I've taken many charter flights that began after the operations "dispatcher" had gone home. To meet the requirements, I filed a flight plan with the FAA.
Some operators with big fleets do go beyond what the FAA requires. But some don't. Depends on how the Ops Specs are written and what they allow.
I don't know Era's specific company policy, but I'd imagine that they monitor their aircraft pretty closely and start looking for an aircraft within 5 minutes or so of his planned ETA. In this case, the ship was 8 miles from the destination, so he was pretty close. From the NTSB report, it seems to me that a search was initiated fairly quickly. I see no indictment of the operator's procedures. Sadly, as happens so often in the helicopter world, even if an all-out search had been initiated immediately at the point of lost contact, it would not have mattered for the pilot.
Why did the pilot appear rushed? In Alaska? Pushing sunset? Yeah, I would have probably appeared rushed too; I don't like flying at night.