Our doors were opened in 1956 by Robert T. Montgomery. Bob was born and raised in Xenia OH.  He was Korean War Veteran in the US Marine Corps, attended the US Naval academy.  He married Dorothy Wilson and had 4 children.  Bob worked at the Ray Cox Insurance Agency and founded Montgomery Insurance in 1956. 

Due to covenants, Bob moved his agency to Beavercreek when he left Ray Cox Insurance.  Then in 1962 he purchased the Brote Insurance Agency in Fairborn OH.   In 1965, Bob added a partner who had been his banker, Phillip Benson.  Phil was the manager at Xenia National Bank.  The agency became Montgomery-Benson Insurance Agency, Inc.  The new partnership purchased the building at 114 S. Detroit St. in Xenia, OH and consolidated all offices  into this facility.  The partnership thrived with Phil managing the operations and Bob focusing on sales.  Bob began to expand his expertise into life insurance and financial services setting the agency apart from most of their competitors who handled mainly home, auto and business insurance.

The agency continued to grow.  In the early 1980’s Phil Benson retired and Bob needed more manpower to handle the growth in sales and operations.  David Mathias was added as an Account Executive and was very successful in sales and community service. Later in the 1980’s Bob hired his two sons.  Brad Montgomery worked for The Travelers in commercial underwriting and Eric Montgomery who also worked for The Travelers in financial services. With this experience a great team was created.  The Travelers, Ohio Casualty, Shelby Mutual, Progressive, Blue Cross/Blue Shield and American Community were the primary insurance companies represented at that time.  The agency continued to grow and prosper in all areas for Property/Liability, Health and Benefits and Financial Services.

Richard Montgomery, Bob’s brother, worked with the agency in the 1960’s and then formed his own agency.  Several mergers later his agency was called Montgomery-Pidgeon Insurance.  In the late 1980’s it became apparent that the two agencies may be much better off by combining forces.  Dick could use the resources of a larger agency and Bob could use new markets like The Cincinnati Insurance Co.  This merger was like no other.  Not only did Bob and his brother Dick reunite family, the agency also took a monumental leap in establishing itself as a prominent provider of financial services and group benefits in addition to the standard lines of home, auto and business insurance.  The agency decided to departmentalize by product line.  Instead of account executives being a jack of all trades and master of none, they became specialists in their own area of expertise.  The Account Executive specialists would truly understand their product line.  This specialization provided a knowledge base that could best serve their clients’ needs.  While the financial services and group benefits departments became an increased focus for the growing agency, the property/casualty department became even stronger with the addition of Cincinnati Insurance Company. 

In 1996 Jim Saner joined the firm.  He worked for The Cincinnati as a commercial underwriter.  Jim’s experience along with his operational and technical skills became invaluable to the agency.  Jim is now a principal of the agency.

In 2002, Montgomery Insurance and Investments purchased the Gerard Insurance Agency of Jamestown, Ohio.  Anne Gerard came on as an Account Executive and served her clients and community well before retiring in 2009.  This agency acquisition allowed Montgomery Insurance and Investments to gain a larger presence in eastern Greene County and added a significant book of farmowners business.  The professional and well experienced staff coupled with the new markets of Westfield and Auto Owners Insurance companies added new quality insurance programs to offer clients and created one of the largest and most diversified insurance and financial services firms in Greene County.  In 2003, Montgomery Insurance and Investments continued to show their support and commitment to the Jamestown community by renovating both the exterior and interior of their office building on the corner of Washington and Limestone Streets.

In 2008 Brad Montgomery’s daughter Blair Davis joined the firm.  She strengthened the family owned agency by bringing her experience as a commercial underwriter with The Cincinnati to the Commercial Lines Dept.  Her enthusiasm and commitment has made an impact on the agency and community.

In 2011 Montgomery Insurance and Investments added a 4th department providing tax preparation services to their clients.  CPA Scott House joined the firm.  Scott has over 40 years experience as a CPA specializing in tax preparation. He has grown the Tax Dept. significantly and built many new relationships in his short time with the agency.  A new family member joined the firm in 2013.  Charlie Davis is Brad Montgomery’s son in law and will be the future of the tax preparation department and serve as CFO for the agency.

Montgomery Insurance and Investments celebrated their 50th year in 2006.  The strategy, talent and knowledge base are in place to last another 50 years serving Greene and surrounding counties.  The focus of the agency will continue to be world class customer service and commitment to the individuals, businesses and communities they serve.