Our Team

Ann Evans - Sales & Service

aevans@OakPointIns.com

Ann works in our California location and has worked alongside Judi Sterling for several years. Ann started in the Insurance Industry back in 1980 and holds her Property & Casualty License. She brings a wealth of experience and specializes in Personal Lines. Ann is friendly and works hard to service our clients. Ann is a lifelong St Mary’s County resident and calls Lexington Park home. When asked what she likes most about working at OakPoint Insurance, Ann says, “I like working with the clients; many are like family.” When Ann is not busy working, she enjoys spending time with her family, music and reading. Get in touch with Ann!


Patrick Haley, CLU, CLCS - President

phaley@OakPointIns.com

Patrick primarily works from our Leonardtown location and is licensed in Property & Casualty and Life Insurance. Patrick also holds his Securities 6, 63, 26. Aside from managing the day to day operations, Patrick specializes in Commercial, Farm and Life Insurance solutions. He has been in the Insurance Industry since 2003 and had many agency and corporate roles throughout his career. Patrick was born in Leonardtown and raised in St. Mary’s County. Outside of OakPoint, Patrick enjoys spending time with his family, fishing, and anything outdoors. Patrick volunteers and coaches youth and high school athletics. He, his wife, and two children reside in Leonardtown, MD. Get in touch with Patrick!


Jessie Leone - Sales & Service

jleone@OakPointIns.com

Jessie, originally from Chesapeake Beach, works from our Leonardtown location and specializes in Personal Lines and outstanding customer service. She holds both Property & Casualty and Life Licenses and enjoys working to take care of her clients’ needs. Jessie has been in the Insurance Industry since 1980 and had many roles throughout her career, including sales, service and underwriting. When asked what she likes best about working at OakPoint Insurance, Jessie says, “Building long term relationships with clients through customer service.” When Jessie is not busy taking care of our clients, she enjoys spending time with family and shopping. Get in touch with Jessie!


Ellen McKisson - Customer Service

emckisson@OakPointIns.com

Ellen works in our Leonardtown office. She started her Insurance career in 1983 and has provided excellent customer service ever since. Ellen takes great care of our clients. When asked what she likes most about working at OakPoint Insurance, Ellen says, “The people are what I like most, the coworkers and the clients.” Ellen lives in Lusby, MD and when she’s not providing outstanding customer service, Ellen enjoys gardening and walking when weather permits. When the weather is not so nice, she loves to cook and read. Get in touch with Ellen!


Kendra Moore, ACSR - Sales & Service

kmoore@OakPointIns.com

Kendra works from our California location and specializes in Personal Lines and Life Insurance. She holds both Property & Casualty and Life Licenses and enjoys working to take care of her clients’ needs. She has been in the Insurance Industry since 2013. When asked what she likes best about working at OakPoint Insurance, Kendra says, “I enjoy working for our Agency because we work as a team.” Kendra lives in Lusby, MD and when she is not busy at OakPoint, she enjoys going to the beach and paddle boarding the waters of Southern Maryland. Get in touch with Kendra!


Kim Rector - Sales & Service

krector@OakPointIns.com

Kim works in our Leonardtown office. She started her Insurance career in 2006 and specializes in Commercial and Farm accounts. She is well equipped to handle Personal Lines as well. Kim is friendly and enjoys taking great care of our clients. When asked what she likes most about working at OakPoint Insurance, Kim says, “The relationships we build with people, both clients and coworkers. We work to positively affect people’s lives and our community.” Kim calls Lusby, MD home and when Kim is not busy managing accounts, she enjoys hiking trails and kayaking. Get in touch with Kim!


Judi Sterling, LUTC - Agent

jsterling@OakPointIns.com

Judi works in our California office. A lifelong St. Mary’s County resident, Judi started her Insurance career in 1985 and owned and operated her Agency in Callaway before teaming up with OakPoint. Judi is a wealth of knowledge in Personal, Commercial and Life Insurance, but her best attribute is caring for her clients. She enjoys providing exceptional customer service and greets all clients with a smile. When asked what she likes most about working at OakPoint Insurance, Judi says “Having friendly workmates is what I like most about our Agency.” Judi lives in Dameron, MD and when she is not busy taking excellent care of her clients or sitting on a board, she enjoys time with her family, especially grandchildren. She also loves cozying up to a good book. Get in touch with Judi!


Melanie Weekley, CLCS - Sales & Service

mweekley@OakPointIns.com

Mel works in our California location and specializes in commercial and personal lines. Mel was born in Southern Maryland and Virginia Beach is where she calls home. Mel began her insurance career in 1999 and her experience and knowledge are a huge asset to OakPoint. She is licensed in Property and Casualty and her experience suits her very well for the agency sales environment. When asked what she likes most about working at OakPoint Insurance, Mel says, “The ability to team up with other knowledgeable agents who have definitely become a second family. We support each other professionally and in personal times of need.” In Mel’s spare time she enjoys crabbing, fishing, going to concerts and spending time with her son. Get in touch with Mel!


While our offices are located in Maryland, we serve all across the following states: Maryland, Texas, Virginia, DC, Pennsylvania, North Carolina, and Ohio.