14. Insurance, Leadership & Legacy with Dottie Chalmers Cutler

In this episode of Housing Matters, Matt Pouliot is joined by Dottie Chalmers Cutter, Chief Operating Officer of Chalmers Insurance Group and a fourth-generation leader of one of Maine’s most respected family-owned businesses. Dottie shares her expert insight on the evolving landscape of home insurance—why premiums are rising, how national disasters affect local rates, and what homeowners really need to understand about their policies. From avoiding costly escrow mistakes to knowing what’s actually covered in a flood, this episode is packed with must-know information for buyers, sellers, and property owners alike. But this conversation goes beyond insurance. Dottie also dives into her leadership philosophy, her passion for coaching over managing, and how she’s transformed the culture at Chalmers through recognition, mentorship, and handwritten notes that make a lasting impact. Whether you're a homeowner, real estate professional, or just love a good Maine success story, this episode is full of wisdom, humor, and practical advice.   🎧 Learn more about Chalmers Insurance Group: https://www.chalmersinsurancegroup.com 📩 Contact Dottie: [email protected] 📱 Follow us on Instagram @housingmatterspod