Caswell Advisory Group
Gregory Caswell
Greg co-founded CAG in 2008 and has since shaped the firm into an advisory practice focused exclusively on the underserved lower middle market, representing business owners of companies valued between $5 million and $25 million, with EBITDA of generally $1M to $3M, across a range of industries. With every new client, Greg’s goal is to build a strong working relationship and execute a tailored marketing and sale process that delivers the best possible outcome while protecting confidentiality and managing deal risk. He has also cultivated deep relationships across the New England transaction community, including investment banks, commercial banks, law and accounting firms, private equity and private investment firms, family offices, and financial advisory firms.
Before founding CAG, Greg built his career in commercial banking, ultimately serving as President and CEO of Coastal Bank, a publicly traded institution based in Portland, Maine. There, he led the bank through a financial crisis, guiding it from an FDIC cease-and-desist order to a full turnaround and successful sale that generated a 31.8% IRR for post-reorganization shareholders. He entered the M&A advisory field in 2005, three years before co-founding CAG.
In addition, he has served on several nonprofit boards, including six years on the Maine Board of Overseers.
Kristen Miale
Kristen joined CAG as Managing Director in 2024. She spent more than a decade as the president of Good Shepherd Food Bank, leading the organization through several transformational growth periods. While at the Food Bank, she grew revenues from $25M to over $100 million, centered its mission on nutrition and equity, and increased distribution from 10M to over 35M meals annually. She was the co-founder of Harvesting Good, a Maine-based vegetable processing company. Prior to her non-profit work, Kristen worked for over a decade as a financial and strategic advisor. She was a senior advisor to a family office overseeing micro- and small-call public and private equity investments and served on the leadership team of a start-up consumer catalog and e-commerce business. In her early career, she served as an advisor to family-owned businesses, where she was a certified business appraiser and provided strategic and ownership transition consulting. She received her undergraduate degree in computer science from Boston College and a master's in business administration from Boston University. She has served on several non-profit boards and community advisory councils and currently serves on the boards of Focus Maine and MEMIC.
Everett Eaton
Everett joined CAG as a senior advisor in 2025. He spent 40 years in commercial lending most recently as the New Hampshire Market President for TD Bank. In that capacity he was responsible for the community and small business lenders in NH. For most of his career he focused on working closely with lower, middle market companies with revenues of $10MM-$75MM to provide creative financing solutions. These included national franchisee groups, importers with complex asset -based lending needs, and major regional retailers, among many others. He provided senior debt in leveraged M & A transactions that included government guarantee programs, tranches of seller financing, and equity rollovers. Everett continues to be active on the Economic Development Commission for the City of Portsmouth, NH where he has resided for many years.
Eric Prouty
Eric affiliated with CAG as Senior Advisor in 2023. He has spent more than 20 years as an equity research analyst in asset management and investment banking covering companies in the industrial and manufacturing sectors and was one of the first analysts on Wall Street to focus his coverage on the then emerging sustainability sector. He is currently a partner at the investor relations and capital markets advisory firm AdvisIRy Partners and is a member of the Board of Directors of Hudson Technologies. Eric also is a Trustee and Treasurer at the Hancock Shaker Village.
Industry Partners
In addition to the core team, CAG has a network of outside associates with strong skills in specific areas, including market research and industry/sector analysis, who are called upon on an as-needed basis.
When it comes time to sell a business, including the development of creative transaction solutions, the Caswell Advisory Group provides business owners with a resource that is fully committed to bringing about a successful sale while navigating as smoothly as possible through the business sale process.
Caswell Advisory Group is a sell-side M&A firm representing business owners in Maine and throughout New England. We manage the full sales process for companies with values between $5 million and $25 million.