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We Believe In You.

The people youre about to meet are in a league all their own.  Their knowledge of the industry is unmatched, their expertise and wisdom are exceptional, and they are some of the most highly-qualified and well-respected people in the business.

Were incredibly proud of our instructors for these reasons and many more.  But theres one unique quality they each have that sets them apart.

They care deeply.

When you register for a class at IIAV, youre signing up for excellence.  Youre setting yourself apart and deciding that learning, and growth are not destinations, but a journey well-worth taking.

As you make your way along this journey, you have our team with you the whole way.  Theyre the best at what they do, and not to mention, some of the best people we know.  We couldn't be prouder of them and we cant wait for you to get to know them.

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Bill Bolling

Bill Bolling was born and raised in the coalfields of southwest Virginia and southern West Virginia.  He was the first member of his family to attend college, graduating in 1979 with a BA degree in Political Science from the University of Charleston.

In 1981 Bill and his wife, Jean Ann, moved to Mechanicsville in Hanover County to put down roots and start their family.  Bill spent his early years working on the carrier side of the insurance business.  He was employed by the Aetna Casualty and Surety Company and the Reciprocal Group, where he specialized in providing professional liability insurance to health care providers.  In 2003 Bill moved to the brokerage side of the insurance business, serving as a producer and Client Executive with RCM&D.

Bill also has a distinguished career in public service in Virginia.  He served as a member and Chairman of the Board of Supervisors in Hanover County and then spent ten years in the Virginia State Senate.  In 2005 Mr. Bolling was elected to serve as the 39th Lieutenant Governor of Virginia.  He was reelected to that office in 2009.  Mr. Bolling has the distinction of serving as Lieutenant Governor with a Democratic Governor, Tim Kaine; and a Republican Governor, Bob McDonnell. 

Following his service as Lieutenant Governor Mr. Bolling returned to RCM&D and served as Managing Director of the firm’s Virginia insurance operations for five years.  In the fall of 2018, he left his career in the insurance industry behind and accepted a teaching Fellowship at James Madison University, where he taught government, politics, public policy and leadership.  Mr. Bolling is currently continuing his focus on teaching at George Mason University and Virginia Commonwealth University, and he also teaches professional courses for the IIAV.

Bill Bolling is married to his wife of 42 years, Jean Ann, and the Bolling’s have two sons, Matt, who graduated form Virginia Tech in 2006; and Kevin, who graduated from JMU in 2010.  Bill and Jean Ann live in Mechanicsville in Hanover County.


Robert N. Bradshaw, Jr., MAM

Bob Bradshaw is the President & CEO of the Independent Insurance Agents of Virginia and joined the Association in May of 2001.

As the IIAV President & CEO, Bob is responsible for the overall operations of the association including all member service and support programs.  He also serves as the industry-agent lobbyist representing and supporting member interests at the General Assembly in Richmond, Virginia.  As the IIAV Chief Executive Officer, he also serves on the boards of IIAV's for-profit subsidiary, the Virginia Financial Services Corporation which handles all of IIAV's member insurance programs and IIAV's educational foundation the Virginia Association of Insurance Agents.

Bob has over 30 years of experience in association and voluntary organization management.  Prior to joining the staff at IIAV he worked with a number of business organizations in Washington, DC including the Associated Builders and Contractors, the National Society of Public Accountants and the National Association of Insurance and Financial Advisors.  He has completed advanced studies at George Washington University where he received a Masters Degree in Association Management through the School of Government and Public Administration.  Bob is active in and past president of the Virginia Society of Association Executives and in 2012 received the VSAE CEO of the Year Award.  Bob has also served for five years on the Legislative Evaluation Committee for Virginia FREE a non-profit organization that promotes a strong business environment in the Commonwealth of Virginia.

Prior to his Masters, Bob received a BA degree in Political Science/History from Lynchburg College in Lynchburg, Virginia.  A native of the Hampton Roads area of Virginia, Bob and his wife Susan reside in Mechanicsville, Virginia.

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Bill Anderson

Bill has been teaching insurance for about 40 years.  He has taught in 45 states and has written for trade journals over the years.  He was at one time the Director of Education for the IIAV and also the VP of Education for the IIAA.  For 6 years he hired, trained and mentored sales people from all over the US for Wells Fargo Insurance Services.  Today Bill is enjoying retirement but still enjoys sharing his knowledge with people in the industry.  


Carlton L. Gill, Jr., CPCU, ARM, CLU, CRIS

Do you know all that you should about the insurance business? I don't. One of the reasons I have taught insurance classes (for IIAV since 1994) is that I learn; both from course material and from the students. I use examples extensively in my classes and this helps everyone to remember the material.

After graduating from Old Dominion University (and while taking MBA classes), I started self-studying CPCU classes. I realized the importance of knowledgeable instructors and upon completion; I started teaching CPCU classes in the Tidewater area. I have been teaching ever since then.

Professionally, I am a producer for Towne Insurance Agency (to whom we sold the Chapin Agency in 2011 ). I work in Newport News but have clients all over the country.

Outside the industry, I am married to a very tolerant woman. We have two grown children and two grandchildren. (Grandchildren are much more fun!)
Because I don't have enough stress in my life, I play golf. Since I am not verygood at it, I really enjoy boating and fishing.

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Gary R. Reinhardt

Gary R. Reinhardt is a partner in the Mid-Atlantic law firm of KPMLaw, based in Richmond, Virginia.  He is an AV-rated attorney with a practice concentrating in insurance coverage, insurance fraud and complex liability defense.  In 2013, he was appointed General Counsel to the International Association of Special Investigation Units and also serves as General Counsel to the Virginia Chapter of the International Association of Special Investigation Units, a position he has held since 1997.  He is also a member of the steering committee and a faculty member of the Virginia State Police and Commonwealth's Attorney Services Council “Red Flag" Program, a training program teaching about insurance fraud to prosecutors, law enforcement and SIU.   He was honored to be selected to both the Virginia Super Lawyers and named to the Virginia Business Legal Elite. 

Gary lives in Midlothian, Virginia, with his wife, and they are the proud parents of two employed adults.  He is President of the Moorefield Owners' Association and a certified therapy dog handler in the Caring Canines organization.


Brian Ross

Born in Roanoke, VA in 1981 and raised in Christiansburg, VA. Obtained business degree at Radford University in 2004 and married wife Eleanor Ross in 2004. Currently residing in Powhatan, VA with Eleanor and two daughters ages 16 and 12. Hobbies include weightlifting and fitness, music and 1980's movies. Current owner and president of WA Watson and Sons Insurance Agency, which is currently celebrating its 100th anniversary."


Joe Hudgins, CPCU

Joe Hudgins graduated from the University of Richmond with a BA in History in 1968. After teaching 6th-grade world geography and 7th-grade history, English and literature for one year, he went to work in the P&C insurance industry in Virginia in February of 1970. During that time he worked primarily in the underwriting area for Virginia Mutual Insurance Company, Crum & Forster Insurance Corporation and Alfa Alliance Insurance Company, retiring in 2008. That same year he went to work for IIAV as a technical consultant, CE teacher, and state lobbyist. Although he "retired" from IIAV in 2012 he still teaches for them, is one of their state lobbyists and works 2 days a week as a technical consultant.

During his time in the insurance industry Joe earned the CPCU designation, obtained a Virginia P&C agent's license, was a member of the Virginia "I" Day Board, and was a  member and chairman of the Virginia Property Insurance Association Underwriting Audit Committee and a member of the Virginia Property Insurance Association Board of Directors.

Currently, he is a member of the Virginia Insurance Continuing Education Board of Directors and serves as chairman of that board's education committee. He also volunteers one day a week at the Virginia War Memorial as an assistant to their curator. 


Douglas M. Palais

Doug is a seasoned trial lawyer and counselor with 35 years of experience.  Doug concentrates his practice in Professional Liability; Errors & Omissions Defense of Insurance and Securities Professionals; Directors & Officers Liability Defense; Securities Litigation and Arbitration; Insurance Coverage and Defense;  Legal Malpractice Defense and Financial Institutions and Securities.  For decades, he has concentrated on defending a wide range of claims against professionals, including insurance licensees, attorneys and securities professionals.  His practice includes the representation of insurance agents and agencies; law firms; securities broker-dealers, registered investment advisers, and individual securities brokers.  Doug is regularly listed in The Best Lawyers in America in the fields of Insurance, Securities Litigation, and Capital Markets.  He has also been recognized as a Virginia "Super Lawyer" in the field of Insurance and Securities Litigation.

He has tried dozens of jury trials, bench trials, and arbitrations in Virginia and in other jurisdictions.  In addition to trying cases in courts and before arbitration panels, Doug has extensive appellate experience in Virginia and in the United States Court of Appeals for the Fourth Circuit. A long-time member of the Virginia State Bar and the District of Columbia Bar, Doug has also handled cases in North Carolina, Tennessee, Georgia, Oklahoma, Texas and Colorado.  He has also served as lead counsel for institutional and individual defendants in major multi-district cases involving insurer insolvencies and alleged securities fraud.

Doug's practice includes handling regulatory issues before federal and state regulators, including the Securities and Exchange Commission, the Financial Institution Regulatory Authority and a host of state securities and insurance regulators.  He is a 1978 graduate of Northwestern University School of Law, where he was Notes & Comments Editor of the Journal of Criminal Law and Criminology and an Instructor in Legal Writing.


Annette Winston

Annette holds an Associate in Science, AS, Career Studies Certificate from J. Sargeant Reynolds Community College and has numerous sales and negotiation advance sales training seminars under her belt.

Annette is a Senior Flood Territory Manager and an IIAA National Flood Endorsement Coordinator. She has seventeen years' experience in the Flood Department of Selective Insurance Company as a Senior Territory Manager. Annette is skilled in all facets of flood underwriting, education, and marketing. She is your go-to resource for understanding the ever changing NFIP rules and regulations. She is a current instructor in VA, MD, DE,DC,WV,KY,NC,PA, AND NY.

She also has 14 years' experience in the Property & Casualty Industry including underwriting, marketing knowledge, program and product development, coverage training, and planning skills.

Annette has been married to Donald Winston for 38 years and they have two adult children.  In her spare time, she likes to travel and collect "shot glasses" of her new adventures. Currently, she is 13 away from completing her 50 states collection.

If you are interested in instructing for IIAV or have questions about instructing, please contact Anna McEachern, Director of Professional Development and Events .