Meet the McCool Team

Bill McCool

Granddad, Fitness, Gardener, Cook, Model Train Enthusiast & Owner.

Bill joined the family agency in 1984.

He is currently the owner and President of McCool Insurance.

He studied Insurance at Eastern Kentucky University where he met his wife Docia. Born and raised in Elkton and is the proud father of three sons Will, Wes, and Joe, and his grandson Camden.

Enjoys gardening, bass fishing, exercising, cooking, and an occasional round of golf. He is currently constructing a new O Gauge model train layout in his basement.

Meet Bill

Docia McCool

Wife, sister, mom, Grandma Doe, Animal Lover, Fitness and Fashion Enthusiast & Book Keeper

Email Docia

Docia has had her Maryland Insurance License for over twenty-five years and is currently the book keeper for McCool Insurance.

She is from Louisville, Kentucky; but married her college sweetheart in 1985 and has lived in Maryland ever since.

She has 3 sons, 2 grandsons and 1 granddaughter. She loves spending time playing and going on adventures with her grandkids. She also enjoys going to the gym and volunteering in the community.

Meet Docia

Wesley McCool

Dad, Husband, Hockey, The Great Outdoors & Marketing

Email Wesley

Son of Bill and Docia, Wesley has helped out with our social media over the years while living in south Florida where he was working on yachts. He recently obtained his P&C license, left the sunshine state with his wife Daniela and son John-Wesley and is now our newest full-time employee.

Wesley loves anything outside (especially the mountains), working with his hands, going on dates with Daniela, and teaching his 1-year-old new skills.

Meet Wesley

Lynda (Lyn) Bailey

Girl Mom and Me-Me, loves the beach life, officer manager and Mentor.

Email Lyn

Lyn has been with McCool Insurance for 40 years. She worked in personal lines and commercial lines. Her current position of office manager. Lyn is a wealth of knowledge and enjoys mentoring the newer agents in the office.

In her free time, you can find Lyn at a beach. She enjoys warm weather, salt and sand. Her most prize possession is her family. Lyn can strike up a conversation with almost anyone and enjoys meeting new people.

Meet Lyn

Dorothy Barone

Mother, Mom-Mom, Wife, Hockey fan & Licensed Insurance Agent

Email Dorothy

Dorothy joined McCool Insurance in 2003 and is licensed in Property & Casualty insurance. Having worked in both the personal and commercial lines departments, she enjoys helping clients and building lasting relationships through exceptional customer service.

Outside of work, Dorothy loves spending time with her husband, two daughters, son, daughter-in-law, son-in-law, and growing family of grandchildren. She enjoys camping, caring for her senior rescue dogs, and cheering on the Philadelphia Flyers.

Meet Dorothy

Melinda LaMontagne

Wife, Girl Mom, Chicken Mom, & Licensed Insurance Agent

Email Melinda

Melinda has been with McCool Insurance since 2017 where she obtained her P&C license. She started in the commercial department but has settled into her role as a personal lines agent. Her favorite part of her new position is meeting her customers face to face.

Outside of work Melinda enjoys long days on the boat, cooking dinner with her husband, and spending time with her daughters.

She enjoys fishing and goes deep sea fishing every chance she gets.

Meet Melinda

Kelly Weber

Boy Mom, Nature Lover &
Avid Reader

Email Kelly

Kelly is our newest addition to team McCool. You may remember Kelly working here in the past and we have welcomed her back to continue her insurance career.

In her free time Kelly and her son Travis love to fish, kayak, and hike - they're always up for an outdoor adventure. Kelly enjoys the warm weather and reading a book any chance she can get.

Meet Kelly