Creswell to Rollo: Remaining Local

The American Dream is real, and Terry & Debbie Carroll are the living proof. For many years, Milan, Tennessee (and far beyond) have been blessed by their faithful servant leadership, their willingness to give back, and their unwavering support of all things local via their thriving family business – Creswell Insurance. As the insurance industry has shifted towards centralization and impersonality, the Carroll family has refused to budge in their faithful stewardship of the local business model that has made Creswell Insurance an indispensable part of the local business landscape. Their agency is an extension of who they are; their staff are an extension of how they serve, and their clients benefit from the work they do.

As the insurance industry has shifted towards centralization and impersonality, the Carroll family has refused to budge in their faithful stewardship of the local business model that has made Creswell Insurance an indispensable part of the local business landscape. Their agency is an extension of who they are; their staff are an extension of how they serve, and their clients benefit from the work they do.

To ensure that West Tennessee remains at the forefront of what the modern free market makes possible for insurance solutions in 2026, Terry & Debbie have been quietly searching for the right opportunity to expand their agency’s capabilities while simultaneously fortifying their truly Local business for generations to come. The solution to that uniquely family-business oriented challenge has revealed itself in the form of another family-owned agency, Rollo Insurance.

Like Creswell Insurance, Rollo Insurance Group is an unapologetically God, Family, and Country-centered agency. Their values are rooted in the conviction that there is absolutely no substitute for a truly local, deeply personal, and truly consultative business model. Today, Rollo Insurance is honored to announce that, effective immediately and under the continued local leadership and watchful care of Terry Carroll, Creswell Insurance is becoming Rollo Insurance – Milan.

Keith Lane (Chief Strategy & Talent Officer) from Rollo Insurance had this to say, “This is an incredibly special moment for bringing together two incredibly special family- owned businesses. Jason Rollo (CEO of Rollo Insurance) and Terry Carroll (Owner of Creswell Insurance) understand that having shared foundational beliefs is the backbone of building a remarkable local business that endures the evolving tests of time. Those beliefs are the launching point from which Milan, Jackson, and the entire surrounding area will begin to see a substantial expansion in what can now be done locally, personally, and in perpetuity. Just as importantly, West Tennesseans have the certainty of knowing that this local business will remain a local business, for good.”