Agency Principles

Brad Montgomery
Brad is a 1980 graduate of Manchester College with a Bachelor of Science degree in Business Administration. He then served as a commercial underwriter for The Travelers Insurance Co. before coming home to the agency in 1983.

Brad is President and majority stockholder of the agency and holds the Chartered Property Casualty Underwriter designation (CPCU). In addition to his responsibilities for overall management, he specializes in property and liability insurance for the diverse commercial and personal client base of the agency. Brad's experience and knowledge allows him to provide creative, competitive insurance solutions along with quality advice and service to individual and business clients. He truly cares about people and community and has a commitment to excellence for the agency.

Brad and, his wife, Tami have two daughters and reside in Xenia. He is active in his church and continues to serve on various civic groups and projects. He enjoys golf, canoeing, fishing and caring for his home and family.


Eric Montgomery
Eric is a 1986 graduate of Rio Grande College with a Bachelor degree in Communications. He began his career as Field Supervisor for The Travelers Financial Services Dept. in Charleston, WV. There he obtained his Life, Health, Annuity and Series 7 Securities licenses. He joined the family business in 1989 and is a principal stockholder of the agency.

Eric is the agency's lead Financial Advisor, specializing in investment and retirement planning for businesses and individuals. He places special emphasis on the comprehensive planning approach encompassing Money Management, Life, Health, Disability and Long Term Care insurance. Eric is actively pursuing industry professional designations.

Eric and his wife Amy have two sons, Kent and Evan, and reside in Xenia. He is active in his church and is civic-minded, giving time and effort to various community projects. His hobbies are golf, gardening, swimming, and spending time with his family. Eric's friendly nature and commitment enables him to build excellent business relationships with his clients.

Eric Montgomery is a registered representative and investment adviser representative of Tower Square Securities, Inc. and is licensed in AL, CA, CO, FL, IL, IN, KY, MA, MI, MO, NC, OH, PA, VA, VT, and WI for the sale of security products.


Roy Montgomery
Roy is a 1977 graduate of Wright State University with a Bachelor degree in Management. He received his Masters of Business Administration (MBA) in 1978. Roy has been with the agency since 1983 and has worked in production, operations, accounting and financial services. He is presently the manager of the Financial Services Department and also assists the financial advisors with case preparation, research and analysis.

Roy has obtained the professional designations of Chartered Life Underwriter (CLU®) and Chartered Financial Consultant (ChFC®) from the American College. He has served as the President of the Dayton Chapter of the Society of Financial Services Professionals and was honored with that organization's coveted Burns Award in 2002. This award is presented annually to recognize outstanding leadership and achievement in the Dayton Chapter as well as the community.

Roy is also a Branch Manager for the Atlantic Division of Tower Square Securities, Inc. (member FINRA / SIPC) and is responsible for the supervision of sixteen registered representatives in Ohio and Indiana.

Roy resides in Xenia. He enjoys Formula 1 racing, college football, reading and cooking.

Roy Montgomery is a registered representative and investment adviser representative of Tower Square Securities, Inc. and is licensed in AL, CA, CO, FL, GA, HI, IA, IL, IN, KY, MA, MI, MN, MO, NC, NJ, NY, OH, OR, PA, RI, TX, VA, VT, WI and WV for the sale of security products.


Jim Saner
Jim is originally from Batesville, Indiana and is a 1995 graduate of Northern Kentucky University with a Bachelor's degree in Management. He came to the agency in 1997 from Cincinnati Insurance Company, where he served as a commercial lines underwriter. Jim earned his Certified Insurance Counselors (CIC) designation in 2005 and became an agency principal in 2006.

Currently Jim oversees the Property Casualty and Health and Benefits departments as well as having all management responsibilities over all day-to-day operations including systems administration and agency support staff. His technical knowledge and management skills provide a tremendous benefit to all of the agency's clients.

Jim resides in Xenia with his wife, Amberly, and their two daughters and son. He is active in his church and enjoys watching and coaching his children in all their activities. Jim enjoys sports of all sorts, as well as caring for his home and spending time with family and friends.


Health and Benefits

Robyn Caupp
Robyn, the agency’s Group Benefits Specialist, was born and raised in Xenia. She graduated from Wright State University with a Bachelors degree in Marketing. She joined the staff of Montgomery Insurance and Investments in 1992. She has obtained the professional designations of Registered Health Underwriter (RHU) and Registered Employee Benefits Consultant (REBC). Robyn’s many years of experience and training have made her a seasoned professional with a unique approach to the Group Benefits field.

Robyn’s knowledge and understanding in working with large and small employers is a great value to the businesses. She develops creative, competitive programs that encompass health, dental, life, vision and disability products. Her understanding of benefits and insurance companies makes her a critical asset to employers and employees alike. Robyn brings her caring attitude and friendly personality to her work and is eager to assist the agency’s clients in any way she can.

Robyn is married with three children. She is active in her church and enjoys sports and caring for her home and family.


Jamie Dolbeer
Jamie is the full time manager of the Health and Benefits Department. She holds a Life and Health license with many years experience in the health insurance industry and has a background in nursing and legal services. Jamie manages the benefits staff and oversees all systems, underwriting, proposals and claim service functions for the department.

Jamie’s knowledge and understanding of the industry and her medical background makes her a valuable asset to our clients in delivering the outstanding service that sets our agency apart from other brokers.

Jamie is active in her church and enjoys participating in her children’s activities. Agency clients can always count on Jamie’s dedication and willingness to serve.


Shelly Bartik
Shelly was born and raised in Chicago, Illinois where she attended Morton College majoring in business. After school, Shelly moved to Las Vegas, Nevada where she worked in the hospitality industry as well as managed an office for a printing wholesaler. She moved to Ohio in 1993 and began accumulating extensive work experience in the medical insurance field from the company side. Her background includes marketing and retention of employer groups and individual policy holders.

Shelly began working for Montgomery Insurance and Investments in the spring of 2008 as a Customer Service Representative in the Health and Benefits department. Her energetic attitude and tireless work ethic make Shelly a tremendous person to help to meet the needs of the employees and employers when dealing with their benefit programs.

Shelly resides in Xenia with her husband. She enjoys traveling, history and spending time with friends and family.


Rebecca Turner O'Bryant
Rebecca has been with Montgomery Insurance and Investments since 2007 as a part-time assistant in our Health and Benefits department. Her duties include processing insurance accounts, preparing proposals and maintaining the computer data base. Rebecca’s organizational and technical skills make her well qualified to support the ever changing and complicated nature of the service issues within the benefits department.

Rebecca earned an Associate Degree from Sinclair Community College and has a Certification from the College of Charleston in Automation Technology. She possesses an extensive background in human resourses and benefits consulting from previous positions prior to joining the Agency.

Rebecca is married with two grown children and is active in her church. She enjoys painting, reading, walking, spending time with her grandchildren and caring for her family.


Financial Services

Don Cain
Don is a 1984 graduate of Wilmington College with a Bachelor Degree in Business Administration and Marketing. Don joined Montgomery Insurance and Investments, Inc. in 2000. He has a Life, Health, Annuity and Series 7 & 66 Securities License and is actively pursuing other industry professional designations.

Don is a financial advisor with the agency and specializes in Investment and Retirement Planning for individuals and businesses. He places special emphasis on the comprehensive planning approach encompassing Money Management, Life, Disability, and Long Term Care Insurance.

Don and his wife Kristi have two children, Nicholas and Megan, and reside in Xenia.

Don Cain is a registered representative and investment adviser representative of Tower Square Securities, Inc. and is licensed in MO, NC and OH for the sale of security products.


Mary Cox
Mary is a 1990 graduate of Xenia High School and studied Office Management at Sinclair Community College. Mary has been with the agency since 2001 and presently serves as the computer operator in the Financial Services Department. Mary's primary responsibilities include maintaining all databases for the department and preparing the financial advisors for their appointments.

Mary holds a Series 6 securities license and helps the advisors and clients process mutual fund transactions. Mary's experience with all facets of the financial services department also enables her to assist our clients with many of their service related requests.

Mary and her husband, Andrew, have three children and they reside in Xenia. She enjoys spending time with her grandchildren and reading.

Property Casualty

Blair Montgomery
Blair returned to Xenia and the family owned agency in November 2008. She is a 2002 graduate of Xenia High School and received her BS degree in Business Administration from Bowling Green State University in 2006. Blair then spent two years as a Commercial Lines Underwriter for The Cincinnati Insurance Company.

Blair’s responsibilities at the agency will be targeted on producing new business for the Property/Casualty division, with a focus on commercial business. Blair, who earned her insurance license in November 2008, is currently involved in formalized sales training and is working towards her Chartered Property Casualty Underwriters (CPCU) professional designation.

Blair resides in Xenia and enjoys spending time on the bike path, fishing, working on here home and attending races at Kil-Kare.


Kristie Dotson Boyer
Kristie has been with the agency since 1991 and is the Personal Lines New Business Account Manager. As a licensed agent, she is responsible for quoting and issuing insurance coverage for all new clients. She is able to provide professional advice on how to make our new clientís premium dollars work more efficiently for them.

In addition to her new business responsibilities, Kristie also trains all new personal lines Customer Service Agents the agency hires. Her expertise and organization in personal insurance allow her to be a valuable resource to agency clients and staff.

Kristie is a life long Xenia resident and a 1990 graduate of Xenia High School. She earned her insurance license in 1997. Kristie and her husband, Tracy, still reside in Xenia and enjoy remodeling older homes.

You can always count on Kristie's dedication, loyalty and willingness to serve.


Kristi Williams
Kris is a graduate of Wilmington High School and attended Southern State Community College. She has many years working in the independent insurance agency system in claims, customer service, and technical capacities.

Kris is the agency's Commercial Account Manager. She is licensed and is responsible for managing all new and renewal business insurance accounts. Her duties include account placement, underwriting and pricing negotiations, classification and rating, proposals and marketing. Kris is skilled at problem solving and is accustomed to searching the standard and specialty marketplace for quality coverage programs for agency business clients. Her knowledge and experience give her the unique ability to tailor insurance packages for clients in a wide variety of industries.

Kris is a mother of two boys. She is a life long resident of Wilmington, OH and continues to reside there. Kris enjoys the outdoors and caring for her home and family.


Andie Fowler
Andie is a full-time, licensed Customer Service Agent in our Jamestown office. She is responsible for processing and servicing farm, homeowner, auto and related personal coverage written by the agency.

Andie analyzes farm and personal loss exposures and can provide proposals on a total account basis. She is responsible for coverage changes, claims, billing questions and general inquires for both farm and personal insurance clients. Andie's knowledge and experience make her uniquely qualified to provide outstanding advice and service to our clients.

Andie is a self-proclaimed farm girl. She is married, with two sons and is a life long resident of the Jamestown area. Andie enjoys working on her family's farm, caring for her horses and traveling throughout the state and country watching her sons participate in rodeo events.


Claudia Cunningham
Claudia is a licensed, full time Customer Service Agent in the Personal Lines Department. She is responsible for processing and servicing homeowner, auto and related coverage written by the Agency.

Claudia can provide advice on coverage and quote competitive premiums. She is also responsible for personal coverage changes, claims, forms, billing questions and general inquiries. Claudia's dedication and training allow her to provide outstanding service to our clients.

Claudia is married with children and grandchildren. She is active in her church and sings in the choir. Claudia enjoys reading, music and caring for her home and family.


Stephanna Seitz
Stephanna joined Montgomery Insurance & Investments in December 2003 as the agency receptionist. In 2006 she was promoted to Personal Lines Customer Service Agent and earned her insurance license in August of that year. Stephanna’s responsibilities as a Personal Lines Customer Service Agent include having daily communication with agency clients about their home, auto and related policies. She is also responsible for handling claims, billing issues, processing endorsements and reviewing policy renewals.

Stephanna is a 2001 graduate of Xenia High school. She and her husband, Steve, currently reside in Xenia, where Stephanna has called home for the majority of her life. They have one child, enjoy taking care of their home, are active in their church and enjoy spending time with family and friends.


Melissa Rinehart
Melissa J. Rinehart joined Montgomery Insurance and Investments staff in January 2004. Melissa, a lifelong resident of Xenia, has a business administration degree from the University of Cincinnati and earned her insurance license in February. She is currently a Personal Lines Customer Service Agent in the Xenia office.

Melissa's enthusiasm in helping clients understand and make informed decisions about their personal insurance programs is a tremendous asset to the agency and her clients. Her main responsibilities as a Personal Lines Customer Service Agent include claims, billing issues, processing client change requests and general inquiries. In this role, Melissa's excellent communication skills set her, and our agency, apart from others.

Melissa enjoys taking care of her home, watching her three children participate in their many activities and supporting her husband, Mark, as Athletic Director of Greeneview Schools.



Agency Support

Tammy Terrell
Tammy joined the agency in June 2006 as the receptionist. Her enthusiastic and friendly personality provides a wonderful first contact for agency clients when calling either of our offices or stopping into the Xenia location. Tammy also provides clerical, database and marketing management support to the entire agency staff.

After living in Cedarville most of her life, Tammy currently resides in Xenia. Tammy is an avid reader, enjoys sports, the ocean, and hanging out with her grown children and one grandchild.

"We had recently moved our insurance to Montgomery. We have been very pleased with the service we have received. It is really nice to have the opportunity to work with professionals that are also personable. Thank You."

- James & Anita Lewis


"We very much appreciate the prompt service we received. I have heard 'horror' stories about other people's response and service from their insurance companies."

- Everett & Ginger Osborne








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Financial Services

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Xenia: 114 South Detroit Street • Xenia, OH 45385 • (937) 372-7646
Jamestown: 1 West Washington Street • Jamestown, OH 45335 • (937) 675-9321
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