For nearly two decades, Caleb Winterburn has dedicated his career to one thing: helping Canadian pilots protect the aircraft they love.

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As Vice President of Aviation Insurance at Covalen, Caleb specializes exclusively in aviation insurance and has helped arrange more than 22,000 aircraft insurance policies for aircraft owners across Canada. From first-time aircraft buyers to experienced commercial operators, he has worked with pilots flying everything from Piper Cubs and Cessna 150s to Cirrus aircraft, business jets, helicopters, floatplanes, warbirds, and commercial fleets.

What makes Caleb different is that he isn't just an aviation insurance broker.

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He is also a Commercial Airplane Pilot and Commercial Helicopter Pilot with experience flying a variety of aircraft throughout Canada. Having flown many different aircraft such as a Vision Jet, L29 Delphin Jet, Robinson 22 and Robinson 44 along with 25 different other machines, Caleb understands aviation from both sides of the cockpit.

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Throughout his career, Caleb has become one of Canada's most recognized aviation insurance specialists, regularly speaking at aviation events, fly-ins, COPA gatherings, and pilot organizations across the country. His passion is helping pilots better understand aviation insurance so they can make informed decisions about protecting one of their largest investments.

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Today, our team and I lead aviation insurance initiatives at Covalen and has been instrumental in developing the Aviators Canada Insurance Program, created specifically for Canadian aircraft owners. The program focuses on education, exceptional customer service, and meaningful coverage enhancements designed around the needs of Canadian pilots.

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Beyond his work in insurance, Caleb is passionate about growing general aviation in Canada. Through educational articles, videos, presentations, webinars, and social media, he shares practical aviation insurance knowledge with thousands of pilots each month. His goal is simple: make aircraft insurance easier to understand and help more Canadians enjoy aviation with confidence.

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Whether you're purchasing your first aircraft, upgrading to a new aircraft, operating a flight school, flying commercially, or simply looking for advice from someone who understands aviation, Caleb believes every conversation starts the same way: by listening first.