Scott Benjamin

About Scott

Scott Benjamin was born on July 8, 1971, in Pawtucket, Rhode Island, a town brimming with blue-collar grit and neighborly warmth. Growing up in a family that believed in rolling up your sleeves and looking out for one another, Scott learned early on that helping others isn’t just a choice—it’s a way of life. That lesson stuck with him, shaping everything he’s done since. Back in 1998, Scott joined the Teamsters Union, and became a working Union Steward for 15 years. He was the guy workers turned to when they had contractual questions or things got tough. He loved diving into the nitty-gritty of union contracts to fight for fair pay, better benefits, and safer workplaces. Colleagues knew him as someone who’d listen, stand firm, and never back down when it came to doing what was right. His knack for connecting with people and solving problems made him a natural leader. In 2013, Scott took a leap into the insurance world, looking for a change and new way to make a difference. He got the hang of personal and employee insurance—Aflac, life, annuities, you name it—pretty quickly. But it wasn’t until 2022 that he really found his groove, focusing on Medicare Advantage and Supplement plans. Scott saw how confusing healthcare is, especially for seniors, and he made it his mission to help folks find plans that fit their lives like a glove, at no cost to them. For him, it’s not about the paycheck; it’s about seeing the relief on someone’s face and the peace of mind they get when they finally understand their options and coverage. Knowing that they have him to call anytime they have a worry or concern is also a huge relief. When he’s not working, Scott’s out on the golf course, chasing his second hole in one. Golf’s his escape—a mix of strategy, fresh air, and good laughs with friends. But nothing means more to him than his daughter, Alexa. Being her dad is his proudest role, and he’s raising her with the same values he grew up with: kindness, grit, and always lending a hand. Whether it’s a heart-to-heart or cheering her on, Alexa’s his world. Now calling Hope Valley his home, Scott’s a familiar face around town, pitching in with local causes and encouraging others to give back. From his days in the union to helping folks with Medicare, Scott Benjamin’s life is all about showing up for people—whether it’s at work, on the fairway, or with his daughter Alexa. He’s proof that a life well-lived is one that lifts others up along the way.