More Than an Agent. The North Shore’s Strategic Partner.
At Longmeadow Insurance, we believe that insurance isn’t just a transaction—it’s the foundation of your financial security. Our agency launched in 2025 with simple premise: families and business owners on the North Shore deserve the same level of sophisticated risk management strategy usually reserved for Fortune 500 companies.
We are an independent agency, which means we answer to you, not a corporate headquarters. We curate the market to find the right coverage for your specific life stage, ensuring that everything you’ve worked hard to build is protected.
Meet the Founder: Tom Firestine
Tom spent over two decades in the upper echelons of the insurance and finance industries, handling some of the complex risks in the world and building an agency he later sold to Hub international foucsed on private equity, venture capital, financial services and technology companies. He launched Longmeadow after seeing a need for community members and businesses to receive that same level of independent expertise and guidance.
Armed with an MBA from the University of Chicago and a BSBA from The Ohio State University, Tom pushes the Longmeadow team to approach insurance with an analytical, “finance-first” mindset. They understands that a policy isn’t just paperwork; it’s a mechanism to transfer risk away from your household balance sheet.
Carrier Partners
Longmeadow launched with a suite of core partners including Erie, Progressive, National General and Lloyds. Our deep industry connections give us access to dozens of carriers and programs we can bring in to drive the best deal for our customers depending on their specific situation.
Deep Roots in the Community
Longmeadow Insurance isn’t just a business; it’s a neighbor. Tom and his wife are raising their two daughters right here in Northfield. We drive the same roads (and dodge the same potholes), deal with the same unpredictable Midwest weather, and care about the same local schools.
Tom brings the values of an Eagle Scout—preparedness, integrity, and service—to every client interaction. Whether serving on local committees or engaging with the Economic Club of Chicago, he is committed to the long-term vitality of our community.
Ready for a Different Kind of Insurance Experience?
Stop hoping you’re covered and start knowing. Contact Longmeadow Insurance today for a review of your risk portfolio.
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Longmeadow Insurance 1100 Central Ave, Wilmette IL 60091
Illinois Insurance License #3003821283
Serving Chicago, Evanston, Glencoe, Glenview, Highland Park, Kenilworth, Northbrook, Northfield, Skokie, Wilmette & Winnetka
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