Princess Anne Office

30386 Mt. Vernon Road

Princess Anne, MD 21853

Our History

Landmark Insurance & Financial Group was first established in 1979 by Charles McClenahan, aka Charlie Mac, in Crisfield, MD.  Even as the business grew, Charlie, served his community as Mayor of Crisfield from 1978-1982, and then served as a Member of the House of Delegates for Somerset, Wicomico, and Worcester Counties from 1992-2003.  As the business grew, Charlie Mac relocated to a more centralized location in Princess Anne, MD, where it remains today. 

Charlie built a loyal and successful team around him, bringing in K. Jill Hall in 1995, and she grew the Health, Life, Employee Benefits, and Financial Planning Departments of Landmark Insurance. “Jill”,as she is widely known and respected within the community, became part owner in 1997.  

As time passed, both of Charlie’s children, Ryan and Heather came to work at Landmark, eventually taking on more responsibility as Charlie prepared to retire.  When Charlie Mac retired in 2014, Jill took over as President and CEO, with Ryan and Heather stepping into Vice President and managerial roles. 

Charlie Mac passed away in 2017 at the age of 76, however, his legacy still lives on, with Landmark Insurance just celebrating its’ 40th anniversary in August 2019. 

A Message from K. Jill Hall, CEO

 “Charles McClenahan, would be very proud of the direction Landmark Insurance is taking as we celebrate our 40th Anniversary. His vision was to always take care of our clients by educating them about how insurance coverages protect them and their families. He also made sure that we were taking full advantage of the latest technology. For example, he was the first in town to have a fax machine. Today, we are constantly researching and educating ourselves about how to use technology so that we can make the business of insurance easier on ourselves and especially to our clients. Yes - there’s an app for that!”