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Kevin’s career started in the mailroom of an insurance company, but it didn’t stay there for long. After several weeks on the job, the branch manager asked whether he was interested in advancing his career as a claims adjuster. Obviously, Kevin said he was. Since then, he has worked his way up into senior adjuster and management positions.


“I just seemed to have an inclination for dealing with people and helping them out,” Kevin said, when asked what that branch manager might have seen in him. Kevin’s strong work ethic and eagerness to learn no doubt also played a role in the fast promotion.


In addition to his invaluable hands-on experience, Kevin has completed numerous courses, seminars, workshops and symposiums to increase his knowledge in insurance and claims. He’s earned his Fellow Chartered Insurance Professional (FCIP) designation.


The personal side

Born in Ireland, Kevin moved to Canada as a young child. He currently lives in Georgetown, Ontario, where he and his wife enjoy the quiet, rural atmosphere. He has three adult children. When he is not working, he enjoys aviation, coin collecting and metal detecting.

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Kevin Flynn, FCIP

Vice President Claims

As DSB’s Vice President of Claims, Kevin Flynn will assist in establishing relationships with clients and developing strategies for improving performance and service. He’ll also mentor and coach the firm’s claim adjusters while fostering excellence, accountability and outstanding professionalism.


“I consider service the number one commodity we can offer” Kevin said. His management style is friendly and approachable, and he makes it clear that he is always available. Aware of the traumatic situations claimants are experiencing, he places a strong emphasis on compassion. As he likes to say, “People won’t care how much you know until they know how much you care.”


Key strengths & specialties

Kevin possesses claims expertise in all lines, including:


  • Commercial
  • Residential
  • Industrial
  • Transportation
  • Bodily injury
  • Accident benefits
  • Reinsurance


He has handled complex catastrophic losses, including those occurring from the Fort McMurray wildfire. He’s proud to have been able to work with those affected, and to know that he could make a positive impact in their lives during a difficult time.


An innovative problem solver, Kevin has a talent for drawing conclusions from hard data, comprehending the big picture and using this information to make decisions. He’s also skilled at dispute resolution, a necessity in claims.


Fun facts

Claims Adjusting Specialty:

High Net Worth


Claim to Fame:

Excellent communications skills


Defining Career Traits:

Success in mentoring young adjusters and challenging them to strive for perfection in what they do


Most Surprising Claim Experience:

Dealing with a difficult client who was later arrested and convicted for murder.


Favorite Canadian Destination:

Vancouver, British Columbia

Peggy’s Cove, Nova Scotia


Unexpected Hobby:

Metal detecting


How to Contact Kevin:

Phone:  647-296-8644




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