About Us


Mission Statement

Provide the highest levels of customer service to ensure our clients’ risks are fully covered. We are a family owned and operated business that believes in serving our customers and the community that we call home.  

 Core Values

 Honesty Loyalty Trustworthiness


Greg Gaylor, CIC, CAIP(Gold Seal), CMIP, LIC



Greg has been in the insurance business for 40 years, working at Gaylor Insurance Agency for the majority of that time. He worked for National Aviation Underwriters from 1981 thru 1988 and then moved back “North” to Roscommon from PTK (Pontiac) in 1989 to work in the family insurance agency.  Greg is licensed in Property and Casualty, Life and Health, as well as having a Surplus Lines License and is also a Licensed Insurance Counselor. Greg has obtained his CIC designation (Certified Insurance Counselor) as well as his CAIP (Certified Aviation Insurance Professional), which includes a gold seal.  Greg is also an expert in marine insurance holding a CMIP designation (Certified Marine Insurance Professional).   Throughout his career he has been active in the Michigan Association of Insurance Agents, having served on their board of directors; as well as serving as Chairman of the Young Agents Council and as a Regional Director for the National Young Agents Council.   Greg has been active in Rotary Clubs in Roscommon, Clarkston and Lansing, and has served as President of the Roscommon Club. He has a Degree in Science from Kirtland College, with a major in Biology & Chemistry.   Greg holds Private Pilots License with Instrument & Multi-Engine Ratings. He spent over 25 years on the Gerrish Township Fire Department, serving the Township as a Fire Fighter and Paramedic. He also spent 8 years on the Gerrish Twp Police Department, as well as a couple years on the Roscommon County Sheriff Department. Most recently he was elected to a 4 year term as the Gerrish Township Supervisor, as well as he served Roscommon County for 10 years as a Deputy Medical Examiner. Greg enjoys boating, skiing (snow & water) – having been involved with the National Ski Patrol for 10 years (serving as the Central Division Insurance Advisor) , bicycling, wine making, restoring muscle cars and just enjoying Northern Michigan.


Greg Gaylor III, CFI, CAWC

Executive Vice President


Born and raised in the Higgins Lake/ Roscommon community Greg graduated from Roscommon High School in 2000. He then attended college at Western Michigan University graduating with a Bachelor’s of Science in Aviation Flight Science in 2005. The degree program included all of the of the ground and flight instruction leading to becoming a Commercial Multi-engine instrument pilot along with Certified flight instructor, instrument instructor, and multi-engine instructor certificates. Upon graduation from Western in 2005 Greg was a flight instructor for Western Michigan’s College of Aviation before being hired to fly for Atlantic Southeast Airlines based out of Atlanta, GA flying the CRJ-200 and CRJ-700 aircraft. Feeling an overwhelming urge to be a part of his generations fight, Greg enlisted in the Navy in 2008 under a special programs contract. After completing a very physically and mentally grueling pipeline training process in the Navy that lasted over a year Greg graduated from NAVSCHOLEOD in April of 2010. After some follow on pipeline schools Greg arrived at EODMU Three in San Diego, CA. Greg spent four years as an operational Navy EOD Tech deploying in support of Operation Enduring Freedom in 2010, 2012 and 2013. Greg is happy to be able to return to the Roscommon community with his wife and two daughters. Greg is a licensed insurance producer and holds a CAWC designation (Certified Authority in Workers Compensation).   



Diana Gaylor, JD, CIC, CMIP

Chief Financial Officer


Has been in the insurance business for over 25 years, beginning with National Aviation Underwriters and then with Gaylor Insurance in 1989 when moving back up North. Diana has a degree in Accounting and Business from Baker College; as well as a Law Degree from Cooley Law School. In the mid 90’s she took a leave from the agency and worked at Applied Systems, out of Chicago as a software trainer and in National Sales for five years. (Applied is the largest provider of insurance agency software in the USA). Diana then came back to the agency and has been there ever since. Diana is licensed in Property & Casualty and has her CIC Designation (Certified Insurance Counselor).



Brian Bile, A&P/IA      

Aviation Risk Advocate  


Brian Bilé started his aviation career in 1985 while working at his Father’s F.B.O. and Part 135 Charter Company in Midland, MI.  Brian opened his first flight school at the age of 25.  Wanting more, Brian moved to California and then on to Hawaii. Continuing his aviation aspirations, Brian worked as a Flight Mechanic on DC-8 and DC-10 aircraft, and then as an Aircraft Maintenance Supervisor with Aloha Airlines.  Since leaving Hawaii in 2007 Brian moved to Las Vegas, NV and continued his Aviation Businesses in Flight Training, Maintenance, and Air Tours.  Brian became a Nevada Licensed P&C Insurance Agent in 2013, and California in 2014. Although no longer operating his Aviation Maintenance and Flight Training Business, Brian still maintains his IA and Pilot Certificate.  Brian Currently works full time selling Aviation Insurance for National Aviation and Marine Underwriters in Las Vegas and as a Maintenance Controller on B737 and B767 ETOPS


Sandra Hatley, ATP, CFI, CFII, MEI 

Aviation Risk Advocate  


Sandra Hatley began her career in aviation first as a flight attendant in 2007.  From there she sought flight school and obtained all necessary certificates and ratings to become a professional pilot.  Today she is an airline pilot, flight instructor and aviation insurance producer.  Her variety of experience thus far is exhibited through her ability to accurately perceive unique individual needs for most aviation services sought.




Amanda Hatley, CISR

Account Executive










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