About Our Agency


Transcend Insurance Solutions, LLC is committed to helping its clients live their best lives in retirement. Owners, Michelle Bacon and Gerald Rupiper have a passion for helping people and providing them with the guidance they need to make educated choices on their Medicare Insurance and other related Insurance Products. The company has its beginning in Green Bay, WI. Where Michelle spent 9 years working for UHC specializing in Medicare Advantage Individual and Group plans. She transferred to Virginia in 2015. After 3 more years as an agent for UnitedHealthcare®, she recognized that her clients could be better served by leaving that single carrier to start her own insurance agency. Transcend Insurance Solutions, LLC. was formed in 2018 by Michelle and she was soon joined by her partner, Gerald. They are committed to finding you coverage that fits your individual needs. Virginia and West Virginia clients will see them visiting their homes and businesses to provide personal one on one service, Michelle and Jerry, typically travel together to meet the needs of their clients. In Wisconsin, their home state, new and existing clients are serviced in person or through phone and video conferences.


Michelle Bacon

Michelle Bacon, Owner and Insurance Broker, has always been focused on helping others. Michelle grew up in Wisconsin and raised 2 sons there. She entered the insurance industry over 12 years ago and has been a Licensed Insurance agent selling to clients in all 50 states, with her focus on this population she has continued her education in gerontology and aging. In 2015, she seized an opportunity for a warmer climate and much shorter winters moving to Virginia. In 2018 she started Transcend Insurance Solutions, LLC which allowed her concentrate on clients in Virginia, West Virginia and Wisconsin. Michelle has an artistic side and likes to create unique pieces of art in many mediums, the projects range from art paintings to Christmas wreaths and everything in between…a recent favorite is creating crocheted hats and other creations. She also enjoys sewing creating clothing items and interior décor. Many of the items she produces make it into the homes of her friends and clients.



Gerald Rupiper

Gerald Rupiper, Owner and Insurance Broker also resided in Wisconsin until he followed Michelle to Virginia in 2015. “Jerry” grew up and lived 45 years on a small island located on Lake Michigan, Washington Island. He is driven to find the correct answers to other’s questions and is known as a “fierce” advocate for his clients. Jerry has one son who still resides in Wisconsin. His career history has its roots in building and repairing recreational yachts and the construction of custom homes. He has been in the Medicare insurance industry for more than 7 yrs. helping clients with their Medicare Advantage and supplement plans. When he is not working, his hobbies range from fabrication and construction with many types of materials; steel, wood, fiberglass, and aluminum, usually having multiple projects on his workbench. Recreation finds him usually on the water boating and fishing. He shares his compassion for others working with Habitat for Humanity in building homes for deserving families.



Karen Manning

Karen Manning has recently joined Transcend Insurance . Karen grew up in Vermont and went to college in Boston. Karen moved to Roanoke, Virginia in 2004 and worked at Advance Auto Parts as a Lease Compliance Administrator. She moved back to Boston in 2012 and met her husband, Bruce. They moved back to Roanoke in 2015 and Karen started working at United Healthcare in 2016 as a Customer Service Representative, where she assisted members and helped members navigate through the complexities and understanding of Medicare Insurance. Karen enjoys working with people and is very compassionate and empathetic and is ready to assist you and help you get into the best Medicare plan that is going to work for you.