Meet The Team

Principle agent Jerry Judge started in the insurance industry in 1990.  He has owned Bayside insurance since 1998.  When not managing the day to day operations at Bayside Jerry enjoys offshore fishing on his boat Double J in the summer and hunting in the winter.  Jerry’s two daughters have recently graduated college and have started careers in engineering.  Jerry and his wife Patty live in Queenstown most of the year but spend a lot of time at their Ocean City home in the summer.

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 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.

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.

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’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.

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.