Our Team
Patrick Haley, CLU, CLCS - President
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 - Account Executive
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!
Jenny Montes - Account Executive
Jenny works in our Owings office. She started her Insurance career many years ago and has provided excellent customer service ever since. Jenny takes great care of our clients. Jenny is also well versed in tag & title work in Maryland. She resides in Lusby, MD and is a great asset to the team. Outside of OakPoint, she loves spending time with my family and three dachshunds, listening to true crime podcasts and creating arts n crafts. When asked what she likes most about working at OakPoint Insurance, Jenny says, "I love the team spirit! Its great that everyone works together for the client's best interest. I feel like I'm a valued part of the team!" Get in touch with Jenny!
Jess Clark, CISR - Commercial Account Executive
Jess Clark works in the California office specializing in Commercial Lines. She has been licensed and working in the industry since 2001. Jess was born and raised in St. Mary’s County. Currently resides next door the home she grew up in Avenue, MD and enjoys spending time with her family and 4 dogs. Get in touch with Jess!
Kendra Moore, ACSR - Account Executive
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 - Account Executive
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!
Kelly Schuman - Operations Executive
kschuman@OakPointIns.com
Kelly works in our Owings office. She started her insurance career in 1989 and holds a Property & Casualty license. Besides handling the insurance needs of the agency’s clients, she also manages the operations of the office in Calvert County. When asked what she likes most about working at OakPoint Insurance, Kelly says “Being part of team which takes great pride in servicing the needs of our clients.” Kelly has just relocated from Calvert County to Millersville, MD and enjoys traveling. Get in touch with Kelly!
Melanie Staff - Account Executive
Melanie Staff Melanie works in our California location. Melanie was born in North Adams, MA and grew up in Pownal, Vermont. Melanie moved to Southern Maryland in 1996 with her husband. In 2007 Melanie began working for Harry Stone as a customer service representative for Stone’s General Insurance. After the death of Harry Stone in 2018, Chris Weller of Monterey Insurance Group purchased the business. December 2018 Melanie became a licensed Property & Casualty agent in order to continue to service and take care of their customer’s insurance needs. Melanie is looking forward to new opportunities and best of all, the opportunity to learn from other Agents that are part of the team. In Melanie’s spare time, she enjoys spending time with her husband, crocheting, painting, firepits and karaoke. Get in touch with Melanie!
Melanie Weekley, CLCS - Sales & Marketing Executive
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!
Chris Weller, CLCS - Vice President
Chris primarily works from our California location and is licensed in Property & Casualty and Life Insurance. Aside from managing the day-to-day operations, Chris specializes in Commercial, Home and Farm Insurance solutions. He has had many agency and corporate roles throughout his career. Chris was born and raised in Frederick County and currently resides in St. Mary’s County with his wife and four daughters. Outside of OakPoint, Chris enjoys spending time camping and boating with his family. Chris volunteers on several boards including the Big "I" Independent Insurance Agents of Maryland and is the King of the Leonardtown Lion's Club. Get in touch with Chris!
We serve all across the following states: Maryland, District of Columbia, Virginia, Delaware, Pennsylvania, Ohio, North Carolina, South Carolina, Texas and West Virginia.
