Allison Dewitt

Background

About Allison Dewitt

I'm what you would call a self-starter. Someone who makes magic from the mundane. An individual with inexhaustible joie de vivre. Growing up outside of Chicago in difficult circumstances, I chose to work full-time at age 14. In fact, I can’t remember a time when I didn’t have a job. I was either babysitting, mowing lawns, removing snow, filing papers in my dad’s insurance office, or selling coupon books door to door. At age 20, instead of going to college, I began building my business through old-fashioned networking and cold calls. My sink-or-swim determination paid off. Before long, I moved to Minnesota and fell in love with the lake life. I joined a thriving insurance company and managed my own clients. As the years went by, I began to envision a fresh and new agency—one that could help individuals and families navigate the unsettled waters of health insurance. So, I founded one. In 2014, I launched Shoreline Insurance Group as if I were launching my vintage 26-foot Skiff Craft—bright eyes on the horizon, strong coffee in hand. Flanked by a savvy crew, I have been sailing my clients to safety ever since. With me at the helm, shopping for health insurance is far from stressful. Some even say it’s fun. I like to laugh, have a gift for simplifying the complex, and am a self-proclaimed bargain shopper. It doesn’t hurt that I know the subject matter inside and out—have ridden the waves of the health insurance industry since 2007. I love diving into the details while my clients stay comfortable on deck. My secret to boundless positivity? Start each day with yoga or a workout with my favorite sailing partner in life; my husband Drew. We enjoy traveling the world and finding adventures along the way. I spend so much time on the water, I even named my cat after the Irish pirate Grace O’Malley. Unfortunately, Grace is afraid of the water, making her a terrible shipmate. She is hoping to learn how to swim from her younger sister Juno, a mini Australian shepherd. In 2023 I rebranded Shoreline Insurance Group to M/Y SHORELINE. Since its maiden voyage, Shoreline has functioned like a ship-like vessel, offering 5-star service to clients like yourself, and navigating them through the waters of health insurance options. For me and my Crew, Shoreline has become more than just a name – it's a symbol of our commitment to providing the very best in insurance & Medicare services. Whatever the day brings, I never veer off-course on my voyage to bring personalized health insurance to you. I hope to see you or your friends onboard M/Y SHORELINE someday!