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Meet the Staff

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Jerry Judge

Agency Principal

Chester/ Easton

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Jessica Boehm

Vice President Life Insurance Sales & Consulting

Direct Line: 410-827-7140

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Jess graduated from Salisbury University in 1988, and spent 28 years with an independent insurance agency in Montgomery County, Maryland. She has been a member of Bayside Insurance since 2017. Jess specializes in Life Insurance, Disability Insurance, Long-term Care coverage and Medicare Supplement Insurance. Customer service is Jess’s top priority. She is on call 24/7 and will meet with clients at their home if needed. She enjoys reviewing coverages with our clients to make sure they are adequately protected and insured under the right program to meet both their short and long-term needs.

In her spare time, Jess enjoys traveling with her husband, Eric. She stays busy with her two Great Danes (who you can occasionally find visiting our Easton office). She also travels to watch her daughter play collegiate field hockey.

Stephani Rader

Vice President of Agency Operations / Agent


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Stephani has been with Bayside Insurance since 2007. She is currently licensed in P&C and L&H. Steph also holds her CISR designation. She continues to work on her education and obtaining other insurance designations. She applies her knowledge to all areas of insurance and enjoys helping clients make good decisions. Her strong drive, and “memory of an elephant”, help her excel in customer service.

Stephani grew up on Kent Island and currently resides there with her son. You are most likely to find her at her sons sporting events cheering him on. She loves football and is a devoted Philadelphia Eagles fan. She also enjoys spending time with her family and friends and relaxing at the beach.

Chris Schindler

Vice President of Sales & Marketing / Agent

Chester & Easton

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From Chris’s youth growing up on Kent Island, to his college years at Salisbury University and to his current residence in Easton, all directions pointed towards a career on the Mid Shore. Chris has taken his local knowledge and a degree in Marketing & Management and has become a successful agent, operating out of both our Kent Island and Easton offices. In addition to his 20 years with Bayside Insurance, Chris’s expertise in both personal and commercial lines, have led to his recent appointment as Vice President.

In his free time Chris can be found fishing, boating and hunting. He also enjoys a good game of golf and spending time with his wife and two daughters.

Pam Spies Mayock



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Bringing with her a wealth of knowledge and experience, Pam has been in the Insurance business since 1995. A dedicated, loyal employee who has seen it all and done it all. She takes pride in the relationships she has established and maintained over the years. Pam is proficient in all aspects of insurance, but feels her expertise is in personal lines. She also enjoys the challenges that come with commercial lines.

In her free time Pam enjoys traveling with her husband and spending as much time as she can with friends and family. She also enjoys community involvement, specifically through the local fire department.

Katelyn Newnam



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Katelyn’s fun and upbeat personality has made her a great addition to the Bayside Insurance team. Joining us in 2018, Katelyn continues to expand her insurance knowledge and is always eager to continue learning. She enjoys personal lines insurance and is passionate about educating clients on their coverage.

When she is away from the office, Katelyn can be found spending time with her family. She enjoys watching her daughter play sports, baking, shopping and taking advantage of everything Eastern Shore living has to offer.

Megan Loveless



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Megan joined the Bayside Insurance team in 2014. With her extensive background in customer service and her passion for working with customers, she was a huge asset to our team right away. Megan enjoys making sure every customer has the coverage they need and takes the time to ensure her customers understand the coverages on their policies. Megan currently holds her P&C license.

Originally born and raised in Annapolis, MD. Megan and her husband decided to call Stevensville, MD. home in 1998. Megan has 3 children, 2 of which are now away at college. Their family is complete with two dogs, two Guinea pigs and a bunny. In her spare time, Megan enjoys yoga, traveling with her family and spending time on the beach and her boat.

Tiffany Thomas



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After recently moving back to Centreville where she attended Queen Anne’s County High School, Tiffany was looking for a career opportunity closer to home. Tiffany is the newest member to our agency. Her previous experience in customer service and management led her to pursue a career in the insurance industry. She is a perfect fit and is always continuing her insurance knowledge.

When out of the office, Tiffany enjoys spending time with her husband and two young children. She is also a Cosmetologist and continues to do hair when she can.

Pamela Godsell



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Pamela has 40 years of insurance experience she brings to Bayside Insurance. She started on the company side, holding various positions and eventually transitioned to the agency side in 1997. She has lived in a variety of states and settled on the Eastern Shore 15 years ago.

When she is not at work, Pamela loves to travel and has gone to numerous Caribbean Islands as well as Africa. She enjoys attending dog shows and shares her home with her pets.