Life Insurance

Provide for your loved ones with a policy that protects them

Employee Benefits

Discover solutions to attract, maintain, and provide for quality employees with our innovative benefit policies

Personal Insurance

Protect your most valuable assets with a personal policy tailored for your life and budget

Business Coverage

Every business runs the risk of unexpected losses. Our comprehensive coverage is designed for your specific needs

 

 

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History of The Winchester Group

The Winchester Group, founded by Gary Nichols in April 2002, is a full service independent insurance agency.

We are extremely proud of the experienced and highly qualified insurance professionals who have joined our agency since its inception. In addition, we have been able to secure contracts with some of the top insurance companies in our industry to include all of our product lines. Our services include consultation and marketing of business insurance, bonding, employee benefits, personal home and auto, business and individual life, individual health, long term disability and long term care.

Here, at The Winchester Group, we truly believe we have something special to offer. Our experience tells us that when it comes to insurance, customers are looking for value. We know that businesses and individuals are looking for the proper level of protection at the most competitive prices. In addition, we know that all customers expect a high level of personal attention and service.

We believe if we are able to exceed those expectations on a regular basis, we should be successful in this business. We are comfortable knowing that our level of success will be determined by your level of satisfaction.

Our entire business is focused around providing quality products and service to our customers. Over time, we hope they will turn to us for all their insurance needs and eventually, we hope to be considered a “Trusted Advisor” by all of our customers.


Gary Nichols

Gary S. Nichols
President

Gary has been helping businesses and individuals with their insurance programs for more than 33 years. The first five years of his insurance career were spent as a claims adjuster in the Tidewater Virginia area, where he gained valuable experience in handling a variety of insurance claims for businesses and individuals.

During the last 28 years, Gary has specialized in designing and servicing insurance programs for businesses in Virginia, as well as other states. He previously served as President of a large, local agency and in April of 2002, was instrumental in bringing together a group of experienced insurance professionals to form a new independent agency, The Winchester Group, Inc.

Gary is a graduate of Wake Forest University and has continued to pursue additional education during his career in the insurance industry. He has obtained several national designations including CPCU and CIC.

Personal quote: "We recognize that consumers can purchase insurance from many different sources. We truly believe we have something special to offer and we are striving to be considered a "Trusted Advisor" by each of our customers."

You may contact Gary at 540-662-9068 x 103 or by email at: This email address is being protected from spambots. You need JavaScript enabled to view it.  or by visiting LinkedIn

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Chad Bales

Chad Bales
Vice President, Insurance Advisor

Chad joined the Winchester Group as a Partner in Jan. of 2004. He has over 20 years of experience in insurance sales and consulting. Throughout his career he has served on various industry advisory councils for both Life and Health and Property and Casualty insurers.

Chad has been part of the Winchester community since 1996. He is a graduate of James Madison University where he earned a BBA degree. Chad has achieved the Certified Insurance Counselor designation and has earned a certificate in General Insurance Studies.

Chad works primarily with corporate clients specializing in commercial insurance and employee benefits. He also provides life insurance solutions to his clients including Individual Life, Key Man Life, Buy Sell Funding, Disability Income, and Long Term Care Policies.

Personal quote: "We enjoy special relationships with our clients. They are not only successful business and community leaders, they are personal friends. At the Winchester Group we understand the importance of this trusted relationship and strive to protect our clients’ assets as if they were our very own."

You may contact Chad at 540-662-9068 x 105 or by email at: This email address is being protected from spambots. You need JavaScript enabled to view it. or by visiting LinkedIn

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Mary Broy

Mary Broy
Vice President, Operations

Mary joined The Winchester Group in January of 2008, with over 30 years of insurance experience. She worked 20 years assisting local businesses with their property and casualty insurance needs. In addition, she worked for an insurance company as an Agency Development Manager. She became a partner of The Winchester Group in 2010.

She obtained her Certified Insurance Counselor designation in 1996 and in 2010, and received the Certified WorkComp Advsior designation. Mary has served on the Agent's Advisory Council for Accident Fund and Loudoun Mutual Insurance Companies. She is the current President of the Insurance Associates of Northern Shenandoah Valley, is a 2013 graduate of the Top of Virginia Regional Chamber’s Community Leadership Program and currently serves on the board of directors for Fremont Street Nursery.

Personal quote: "At The Winchester Group, we are passionate about the personal attention we provide to our customers. We have experienced employees who are dedicated to serving the insurance needs of our clients.”

You may contact Mary at 540-662-9068 x111 or by email at: This email address is being protected from spambots. You need JavaScript enabled to view it.  or by visiting LinkedIn

 

 

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Chelsea Hester
Vice President, Insurance Advisor

Chelsea joined our team in 2007. In January 2013, she became a managing partner at The Winchester Group. Chelsea continues to work with business clients on their commercial property and casualty insurance and employee benefits. She also assists individuals with life insurance and long term care insurance needs. She has achieved the Commercial Lines Coverage Specialist designation, was awarded the Accredited Advisor in Insurance certification and recently attained the professional designation of Certified Insurance Counselor (CIC).

Chelsea is a graduate of James Madison University where she earned a Bachelor of Science degree. She is a 2010 graduate of the Top of Virginia Regional Chamber’s Community Leadership Program. She is active in community civic organizations and enjoys playing golf.

Personal Quote: “At the Winchester Group, we are committed to building lasting relationships with our clients and make every effort to provide exceptional service to meet their needs in a professional manner.”

You may contact Chelsea at 540-662-9068 x 110 or by email at: This email address is being protected from spambots. You need JavaScript enabled to view it. or by visiting LinkedIn

 

 

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Cathy Aikens
Account Executive

Cathy Aikens joined The Winchester Group early in 2006 to implement a client resource program to broaden the company's value-added professional services. This program offers busy managers immediate access to benchmark surveys and statistics, compliance and plan designs, employee communication and education, as well as employer education. Be sure to ask Cathy if you would like to learn more.

Cathy has a Bachelor's Degree in Business Administration with Averett University. In addition, she has over 12 years experience working in the Human Resources field, with specialization in Employee Benefits. Receiving her certification in Professional Human Resources in 2000, Cathy remains current on HR issues by taking continuing education classes.

Personal quote: "I've always had a passion for the world of employee benefits and truly enjoy helping our clients get the most from their programs.”

You may contact Cathy at 540-662-1828 x 106 or by email at: This email address is being protected from spambots. You need JavaScript enabled to view it.  or by visiting LinkedIn

 

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Sue Barnett
Account Executive

Sue joined the agency in August of 2003 and has 28 years of insurance experience, primarily in Personal Lines. Home, Auto, Life, Motorcycle, ATV, and Personal Umbrella Liability coverage are some of the many products she is able to offer as an Account Executive.

Sue holds various insurance designations such as ACSR, AIAM, and CPIW. She is a charter member of The Insurance Women of Northern Shenandoah Valley and remains active in the organization. Sue is also a member in the Kiwanis of Old Town Winchester and has held various leadership positions in the organization. She is also active with The Boys and Girls Club of Northern Shenandoah Valley.

While Continuing Education is an integral part of maintaining ones insurance license, Sue is constantly looking for classes that are relevant to further her knowledge and client service skills at The Winchester Group.

Personal quote: “I believe our client’s needs are first and foremost. I will do my best to assure each client is treated with respect and confidentiality and provide the highest level of insurance knowledge possible. I will strive to not only meet your expectation but exceed it!”

You may contact Sue at 540-662-1828 x 102 or by email at: This email address is being protected from spambots. You need JavaScript enabled to view it.  or by visiting LinkedIn

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Becky Bowers
Office Manager

Becky joined The Winchester group in 2013 to assist with daily operations and the implementation of program enhancements to better serve our customers.

Becky is a graduate of Radford University and has 17 years of accounting and management experience. She and her husband, Joe, reside in her native Winchester and have two children, Lyndsey and Cody.

Personal Quote: “I am thrilled to be a part of The Winchester Group. The kindness and exceptional service that is of utmost importance to our customers is extended to everyone both inside and outside of the office. Establishing and cultivating relationships with customers, vendors and our team is vital to future success.”

You may contact Becky at 540-662-9068 x 114 or by email at: This email address is being protected from spambots. You need JavaScript enabled to view it.  or by visiting LinkedIn

 

 

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Laura Cornwell
Account Manager

Laura joined The Winchester Group in May, 2010, and she has over five years of insurance experience as a Customer Account Executive. Her experience includes servicing, underwriting and marketing commercial insurance accounts. Laura graduated from Frederick Community College in 1999 and is a 2004 graduate of Shepherd University where she earned her Regents Bachelor of Arts Degree. Laura resides in Marshall, VA with her husband and is currently working towards obtaining the Accredited Customer Service Representative designation.

Personal Quote: “I am so happy to be a part of The Winchester Group as it has been the perfect fit for me. I have been successful in making relationships that are not only familiar, but comfortable for everyone involved. My goal as a Commercial Lines Specialist is to gain the trust of my customers and give them more than they expect at all times.”

You may contact Laura at 540-662-9068 x 108 or by email at: This email address is being protected from spambots. You need JavaScript enabled to view it.  or by visiting LinkedIn

 

 

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Marty Crockett

Marty Crockett
Account Executive

Marty started with The Winchester Group as an Employee Benefits Specialist when the business opened in 2002. She has been involved with Employee Benefits for over 15 years and has extensive knowledge in the areas of Group Health, Life, Disability and Dental Plans. She also writes individual Health Insurance, Medicare Supplements and Medicare Part D.  Her knowledge of COBRA and Flexible Spending Plans has given The Winchester Group the opportunity to offer these services to employee benefit customers through a third-party administrator.

Marty is regularly involved with the servicing and selling of Employee Benefits for small and large businesses. She solves complex claims issues, conducts open enrollment meetings and develops excellent working relationships with customers and insurance carriers. She also regularly attends seminars and training offered by the insurance carriers, to remain current on issues and new trends in the marketplace.

Marty is a Past President of NAIFA-Winchester and is a member of the Winchester Society of Human Resource Management.   She is currently serving on the Anthem Blue Cross Blue Shield Broker Advisory Panel for the Northern Region. 

 

Personal quote: "My goal is to provide the best products and customer service to my clients. It is so rewarding to know that I have played a role in obtaining benefits that will protect employees and their families and that they can call me whenever they need assistance."

You may contact Marty at 540-662-9068 x 101or by email at: This email address is being protected from spambots. You need JavaScript enabled to view it.  or by visiting LinkedIn

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Philip Dorsey

Philip Dorsey
Customer Service Representative

Philip joined The Winchester Group in January 2013, and has seven years experience as a Customer Service Representative. Philip currently holds licenses in both Property & Casualty and Life & Health Insurance. He has experience working with Personal Lines coverage as well as Commercial and Life Insurance. In time, he will be working towards earning specific designations to expand his knowledge and skills to better assist the valued clients of The Winchester Group.

 

Personal quote: “I am extremely excited to be a part of The Winchester Group and its incredible team of professionals. Providing the highest level of customer service is vital in this industry and is a trait that is deeply valued and strived for in this agency. I look forward to working together and building quality relationships with each and every client that puts their trust in The Winchester Group."

You may contact Philip at 540-662-9068 x 118 or by email at: This email address is being protected from spambots. You need JavaScript enabled to view it.  or by visiting LinkedIn

 

 

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Teresa Haas
Administrative Assistant

Teresa joined The Winchester Group in January, 2009. She is a native of Upstate, New York and moved to Virginia in 1997. She has a two year degree in Business Management and has over 15 years of customer service experience.

Personal Quote: "Here at The Winchester Group, it is all about customer service. From the moment you walk through our door or talk to us on the phone, we want you to feel welcome and confident in our service. You are not only our client, you are like family."



You may contact Teresa at 540-662-9068 x 100 or by email at: This email address is being protected from spambots. You need JavaScript enabled to view it.  or by visiting LinkedIn

 

 

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Cheryl Hart

Cheryl Hart
Account Manager

Cheryl has lived in Winchester for 25 years. She joined the Winchester Group in March 2004 and has over 25 years of insurance experience with commercial insurance accounts.

Cheryl has achieved the following insurance designations: Certified Insurance Counselor, Associate in Claims, Associate in Account Management, and Accredited Customer Service Representative. She is a Charter Member of the Insurance Women of the Northern Shenandoah Valley.

Cheryl works exclusively with commercial property and casualty clients at The Winchester Group. Her role includes advising clients about insurance coverage, implementing policy changes, handling claims, and discussing accounting matters.

Personal Quote: "Building strong relationships is vital to the success of an insurance agency. The Winchester Group understands this concept well and we take great pride in providing exceptional service to our clients."

You may contact Cheryl at 540-662-1828 x 104 or by email at: This email address is being protected from spambots. You need JavaScript enabled to view it.  

 

 

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Hildred Hott
 Customer Service Representative

Hildred joined The Winchester Group in October, 2008. She is a lifelong resident of Winchester and Frederick County. She is a graduate of Longwood University and has over eight years of experience in the insurance industry. She earned the Certified Insurance Service Representative designation and achieved her Certified Insurance Counselor designation in 2012.

Personal Quote: “The Winchester Group shares my belief in personal and local customer service. I look forward to building relationships with our clients and helping them with all of their insurance needs.”

You may contact Hildred at 540-662-9068 x 115 or by email at: This email address is being protected from spambots. You need JavaScript enabled to view it.  or by visiting LinkedIn

 

 

 

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Mandy Jett

Mandy Jett
Customer Service Representative


Mandy joined The Winchester Group in September, 2011, and she has over six years of insurance experience as a Commercial Lines Account Manager.  Her experience includes servicing and marketing Commercial Lines accounts.  Mandy earned her Bachelor of Science in Business Management and Information Systems from University of Phoenix in August, 2008.  Mandy is currently working towards obtaining the Certified Insurance Counselor designation.

Personal Quote: “The satisfaction of our clients is of utmost importance.  We strive to go above and beyond in servicing our customers and ensuring our clients have the coverage they need.”

You may contact Mandy at 540-662-9068 x 107 or by email at: This email address is being protected from spambots. You need JavaScript enabled to view it.  or by visiting LinkedIn

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Chris Johnson
Insurance Advisor

Chris joined The Winchester Group in January 2009 after running his own agency. He has over 12 years of experience in insurance sales and consulting with the majority of the time working with corporate clients on commercial insurance. Chris holds licenses in both Property and Casualty Insurance and Life and Health Insurance. He has begun working towards the professional designation of Certified Insurance Counselor (CIC).

Chris is a graduate of Old Dominion University. He is a member of The Rotary International. Chris enjoys spending time with his family, playing golf, softball, running and coaching his children’s sporting teams. He and his wife Lara have two children, Catherine and Christian.

Personal Quote: “It is imperative that we foster a partnership with our clients. We understand the trust our clients have put in us and it is our mission to ensure we meet their objectives and frequently exceed their expectations.”

You may contact Chris at 540-662-9068 x 113 or by email at: This email address is being protected from spambots. You need JavaScript enabled to view it. or by visiting LinkedIn

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Howard Morris
Personal Insurance Advisor

Howard joined the Winchester Group in March of 2014, as Personal Insurance Advisor, and has over 12 years of sales and customer service experience. Howard holds a license in Property and Casualty Insurance. Howard is a graduate of James Madison University, where he earned a Bachelor of Business Administration degree. He is active in community and civic organizations.

Personal Quote: “Our client’s satisfaction is fundamental to everything we do. At the Winchester Group, my goal is to develop lifelong partnerships where my integrity and years in customer service combined, yield comprehensive solutions that meet my customers current and future needs.”

You may contact Howard at 540-662-9068 x 119 or by email at: This email address is being protected from spambots. You need JavaScript enabled to view it. or by visiting  LinkedIn

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Sharon Orrison

Sharon Orrison
Account Manager

Sharon joined The Winchester Group in April of 2005. She has over 30 years of experience working in commercial insurance. Additionally, she has achieved the Certified Professional Service Representative designation.

Sharon works exclusively with commercial clients of The Winchester Group. Her role includes assisting customers with claims, taking policy changes, discussing current coverages, and handling billing inquiries.

Personal Quote: "I really enjoy personal interaction with our customers. We greatly appreciate them and strive to show them each time they call."

You may contact Sharon at 540-662-1828 x 109 or by email at: This email address is being protected from spambots. You need JavaScript enabled to view it.  or by visiting LinkedIn

 

 

 

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Angie Wymer
Account Executive

Angie joined TWG in March 2008 and has over 35 years of insurance experience serving the needs of individuals with Home, Auto, Life, Motorcycle, Boats, ATV’s and many other related lines of coverage. She holds licenses in both Property and Casualty Insurance and Life and Annuities Insurance. She has earned the Accredited Customer Service Representative and Associate in Insurance Account Management designations. She is the recipient of the Travelers Personal Lines High Achiever award.

Personal quote: "I like to show my clients that I care about them and their insurance needs. I take time to listen and use my insurance skills and knowledge to offer the best coverage for their unique situation and remain sensitive to the cost. I like to involve the client in the decision making process as it is important they receive the peace of mind that comes from buying insurance. I hope to build a relationship of trust as their insurance agent. I am happy to be a part of the team of professionals here at The Winchester Group - working together to achieve the best for everyone.”

You may contact Angie at 540-662-9068 x 112 or by email at: This email address is being protected from spambots. You need JavaScript enabled to view it.  or by visiting LinkedIn

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Accident Fund (866) 206-5851
ACE (800) 945-7461
Chartis (888) 760-9195
Chubb (800) 252-4670
Cincinnati (877) 242-2544
EMC (888) 362-2255
Erie (800) 542-2250
After Hours: (800) 367-3743
Fireman's Fund (888) 347-3428
Hanover (800) 628-0250
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Hartford (800) 327-3636
Loudoun Mutual (800)752-3458
MainStreet America
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(877) 425-2467
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Progressive (800) 776-4737
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