SIMPSON'S OLDE TOWNE INSURANCE - Key Persons


Chris Simpson

Job Titles:
  • Agent
  • Associate
  • Insurance Agent
Chris is born and raised in Charles County and currently resides in La Plata. He is a graduate of McDonough High School, The College of Southern Maryland, and Salisbury University. After graduating from Salisbury he joined Community Bank of the Chesapeake in their commercial banking division. Chris joined Simpson's Olde Towne Insurance in 2016 and primarily focuses on Commercial, Personal, and Life insurance sales. Chris is very active in the community being a former President of the Charles County Rotary and a current board member of the Charles Regional Medical Center Foundation. In his free time, Chris enjoys playing golf and attending Maryland football and basketball games with his family. Chris is currently planning a December wedding this year with his fiancé, Erin.

Gary M. Simpson

Job Titles:
  • Principal Agent / Owner

Janine Mohler

Job Titles:
  • Associate Agent, Certified Insurance Service Representative
Janine also known as "Ginger" moved to Port Tobacco, MD in 1975. After graduating from La Plata High School in 1979 she started working in the Insurance Industry while attending the College of Southern Maryland. Janine worked for over 34 years as an agent for King E Adkins Insurance. While working in commercial and personal lines servicing she obtained her Property and Casualty license in 1986. In 1991 she earned her Certified Insurance Service Representative (CISR) designation. She also obtained her Notary commission in 1991. Janine has been married to her husband Doug for 36 years. Together Doug and Janine have a son Hunter and daughter-in-law Caitlin Marie who are expecting their first child in August of 2022. In her spare time, Janine is an avid walker and loves to watch her son play baseball. Janine is looking forward to being a "NANA".

Linda Bennett

Job Titles:
  • Associate Agent, Certified Insurance Service Representative
Linda lives in Southern Maryland, she graduated from La Plata High School in 1981. Linda started her insurance career in Annapolis MD in 1985, she left the insurance industry in 1992 to be a stay-at-home mom. When Linda returned to the workforce, she obtained her Maryland Real Estate License working for a local real estate appraisal firm for 8 years before deciding to return to the insurance industry. Linda obtained her Property and Casualty Insurance license in 2002. She has earned her Certified Insurance Representative (CISR) designation in 2008 and Personal Lines Coverage Specialist designation (PLCS) in 2010.

Matt Laidley

Job Titles:
  • Agent
  • Associate
Matt is a native Marylander who moved to LaPlata in 2003 after retiring from the United States Navy after 22 years of active duty service. He is a graduate of Anne Arundel Community College. Matt joined Simpson's Olde Towne Insurance in 2009 and primarily focuses on Personal and Life insurance sales. Matt was ordained as a Permanent Deacon in the Roman Catholic Church in 2019 and is assigned to Sacred Heart Catholic Church in LaPlata, MD. Matt is married with four daughters and eight grandkids. In what little free time he has he enjoys cycling to keep in shape and has completed four 100 miles (Century) bike rides over the last six years.

Taylor Kiessling

Job Titles:
  • Customer Service Representative
Taylor joined Simpson's Olde Towne Insurance in 2022. She is a graduate of La Plata High School, College of Southern Maryland, and University of Maryland. She resides in La Plata with her husband Jake and their baby girl. In her free time Taylor enjoys spending time on the water boating with her family and friends.