Meet Ben Diamond, Shoreline Aviation’s most recent certified flight instructor

When Benjamin Diamond was 16 his dad took him on an introductory plane flight at Norwood Memorial Airport (KOWD).
“I was so enamored, I didn’t even know what to ask. I didn’t know what I didn’t know,” Ben said. “From then on I wanted to know more about it; I had to start learning.”
The Mansfield resident trained for his private pilot’s license – which he earned at 21 in 2018 – at Bridgewater State University’s Division of Aviation Science. Ben flew most of his 1,700 flight hours with East Coast Aero Club at Norwood Memorial. He earned his certification as a flight instructor in May 2023. To do that he needed his private pilot certificate as well as a commercial certificate and successfully complete Flight Instructor Airplane and Fundamentals of Instruction written exams.
Ben recently joined the Shoreline Aviation team at Marshfield Municipal Airport (KGHG) and quickly became busy teaching flight students in the company’s Piper Warrior trainer fleet.
“My overarching goal is to fly for a company like Shoreline, possibly Shoreline, and just enjoy what I’m doing,” he said. “I don’t want to fly as a daily routine. There’s a great atmosphere here, very positive. Everyone enjoys being here.”

Flight instructor Ben Diamond poses with one of Shoreline Aviation’s Pilatus PC-12 fleet aircraft.
Ben hopes to train with Shoreline to fly its Pilatus PC-12 turboprop fleet and move on to their Citation 560XL fleet of jets. His goal is to learn via Shoreline’s Pilot Development Program. That training program received FAA approval last year after a year of development. Shoreline Director of Operations P.J. Flanagan worked directly with the FAA to develop the program, by which established captains would mentor pilots aspiring to fly jets.
In gaining his 1,700 hours of flying time, Ben has flown over much of New England, as far as Eastport, Maine, and to eastern Pennsylvania and southern coastal New Jersey. He has flown mostly trainer general aviation planes such as the Warrior and the Cessna 172. He has also flown the twin-engine Cessna Chancellor and Beechcraft King Air 200 twin turboprop.
Ben can thank his family for at least part of his aviation success.
“My family has always supported me, even with the tough times of flight training,” he said. “Their support allows me to push myself further.”
That lesson is not lost on up-and-coming pilots who could use some words of wisdom from someone who has done it: “Study hard, practice, and watch yourself succeed.”
You can reach Ben at 781.834.4928.
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