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.  

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. He 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.

Geoff Gaylor

Vice President

Born and raised in the Higgins Lake/ Roscommon community Geoff graduated from Roscommon High School in 2007. He then attended college at Madonna University on a basketball scholarship.  After setting Rebounding and Blocked Shot records at Madonna, Geoff was selected to be in the NBA Development League Draft, where he attended several tryouts.   He then pursued a career as a Paramedic with MMR (Mobile Medical Response). After a few years with them he decided follow his fathers and grandfathers footsteps and get into the insurance business.

Geoff then attended Ferris State University and received his Bachelors Degree in “Insurance & Risk Management” – part of that degree was completion of several of the CPCU parts, which Geoff is now pursuing to completion.  Geoff is a licensed insurance producer in Michigan and several other States.   

Diana Gaylor, JD, CIC, CAIP, CMIP

Chief Financial Officer

Diana has been in the insurance business for over 25 years, beginning with National Aviation Underwriters. She joined Gaylor Insurance in 1989 after moving back up North. Diana has a degree in Accounting and Business from Baker College. She also has 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. She is licensed in Property & Casualty and has her CIC Designation (Certified Insurance Counselor).  Diana has also obtained her CAIP (Certified Aviation Insurance Professional) and her CMIP (Certified Marine Insurance Professional) designations.

Asia Wrege


Bio Coming Soon….