Our Team

Ann Evans - Account Executive

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!


Melissa Collins-Gut, CLCS, PLCS  - Sales Executive

mgut@OakPointIns.com

Melissa works in the greater Charlotte, North Carolina market and is licensed in Property & Casualty and specializes in Commercial Insurance solutions. Melissa is well traveled, fifteen years of living abroad. Starting in Canada, her journey then took her family to Bahrain, Hong Kong and finally Singapore. She had some incredible experiences both living and working in various countries and having the privilege to travel all around Asia and the Middle East.  While her original degree is in Immunology, she taught Physics in Bahrain and coached at a local Crossfit gym. In Hong Kong, she continued in the fitness space and worked as a Strength and Conditioning Coach for a few National Teams and as a Women’s Health Coach for a local female only outdoor bootcamp. She continued in the coaching/personal training field when she moved to Singapore. Melissa and her husband have two children, a labradoodle, and a cat. In her spare spare time, you will usually find her cycling or running, reading a good book or baking sourdough bread. Get in touch with Melissa!


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 - Account Executive

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!


Jenny Montes - Account Executive

jmontes@OakPointIns.com

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!


Kendra Moore, ACSR - Account Executive

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!


John "JJ" Raley - Sales Executive

jraley@OakPointIns.com

JJ works in our California office and holds a degree in business from Providence where he played soccer. He holds a Property & Casualty and Life License while specializing in Commercial, Home, Life and Farm accounts.  JJ continues his passion in soccer working with multiple youth groups.  JJ is the head boys varsity coach at St. Mary's Ryken High School and was named WCAC coach of the year in 2021.  He calls Piney Point, MD home and when JJ is not busy providing insurance advice, he enjoys spending time with his wife and daughter. Get in touch with JJ!


Kim Rector - Account Executive

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!


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

mstaff@OakPointIns.com

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!


Judi Sterling, LUTC - Account Executive

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 Leonardtown, 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 & Marketing Executive

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!

reading. Get in touch with Ann!


Chris Weller, CLCS - Vice President

cweller@OakPointIns.com

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.