Sara B. Huddleston
When a client is preparing to sell a business they built from the ground up, they need a lawyer who brings not only legal skill but also empathy, focus, and clarity to the table. Sara is that lawyer.
With a foundation in public interest work and a deep appreciation for the human impact of business transitions, Sara brings a steady and thoughtful approach to complex corporate transactions, especially mergers and acquisitions for closely held and family-owned companies.
Sara works closely with business owners who are navigating critical moments: selling to a private equity firm or strategic buyer, transitioning out of an ownership role, or stepping into retirement. She takes pride in guiding her clients through this high-stakes process—managing risk, reviewing and negotiating deal terms, and helping them make informed decisions about their company, employees, and financial future. Sara understands what’s at stake: when the deal will close, how earnouts are structured, how to reduce exposure to post-closing claims, and what kind of legacy the client wants to leave behind.
Her corporate practice specializes in middle-market M&A transactions, where she advises clients throughout every phase of a sale, from initial structuring and due diligence to closing. She also offers general outside counsel services to corporations and LLCs, managing matters such as unit and stock purchases and redemptions, governance issues, and buyouts of retiring or departing shareholders. Sara regularly forms corporations and LLCs in Massachusetts, Vermont, and Delaware, as well as drafts and reviews operating agreements, shareholder agreements, and bylaws.
Advised on $50 Million Sale of Family-Owned Manufacturing Business
- Represented a multigenerational, family-owned specialty bearings manufacturer in its $50 million stock sale to a private equity firm. Led negotiation and drafting of the stock purchase agreement and all ancillary documents, coordinated closely with buyer’s counsel and the client’s investment banker, and secured representation and warranty insurance to mitigate post-closing exposure.
Counseled on $30 Million Janitorial Services Company Acquisition
- Assisted in the $30 million stock sale of a family-owned janitorial services company to the nation’s largest privately held facility maintenance provider. Managed all aspects of the transaction, including drafting key documents, supporting an F-reorganization, and overseeing post-sale foreign entity registrations.
Supported $62 Million Private Equity Acquisition of Technology Company
- Worked on the $62 million stock sale of a private technology company to a private equity buyer. Drafted transaction documents and coordinated directly with the client and opposing counsel throughout the deal lifecycle.
Assisted in $25 Million Asset Sale of Oral Surgery Practice
- Contributed to the $25 million asset sale of a multi-surgeon oral surgery company to a private equity-backed oral healthcare platform. Drafted ancillary documents and served as a key liaison between client and buyer’s counsel to ensure a smooth closing.
Advising on $14 Million Sale of Engineering and Testing Firm
- Currently representing a closely held engineering and testing firm in its $14 million stock sale to a global strategic acquirer. Drafting disclosure schedules and collaborating with the client, business broker, and legal teams to address employment, transactional, and regulatory considerations.
Leading Purchase of Vermont Dermatology Practice
- Spearheading the $725,000 acquisition of a Vermont-based dermatology practice by a New York physician. Negotiating favorable deal terms and advising on compliance with licensure and healthcare regulatory requirements.
Supported $60 Million Capital Raise for Real Estate Investment Firm
- Worked on a $60 million multi-stage capital raise for a family-owned real estate investment company. Drafted the offering memorandum, managed investor communications and documentation, and ensured compliance with applicable securities laws.
Formed and Structured Business Entities Across Multiple Jurisdictions
- Established numerous limited liability companies and corporations in Massachusetts, Vermont, and Delaware. Drafted foundational governance documents, including operating agreements, shareholder agreements, bylaws, and certificates of formation and incorporation.
Advised Corporate Client on Post-ESOP Stock Redemptions and Governance Updates
- Guided a private engineering firm through a series of stock redemptions following its transition to an employee stock ownership plan (ESOP). Interfaced with ESOP counsel and trustees and updated key governance documents to reflect the company’s evolving structure.
Education
- JD, Boston College Law School, 2017
- BA, magna cum laude, Middlebury College, 2009
Bar Admissions
- Massachusetts
- Vermont
Experience recognized
- Massachusetts Super Lawyers, Rising Stars, 2025
Experience in practice
Women M&A Lawyers at Rubin Rudman are Bucking the Trend
- Henry Sheldon Museum of Vermont History in Middlebury, Vermont, Trustee
- AmeriCorps, Former Community Health Promoter in Shelton, Washington
- HealthCorps, Former Coordinator in Santa Ana, California
- Boston College Law School, Pro Bono Program, Public Interest Designation Fellow—New England Innocence Project, Boston College Innocence Program, Massachusetts Committee for Public Counsel Services’ Innocence Program
Rooted in Vermont, Recharged by Nature
Based in her hometown of Middlebury, Vermont, Sara finds balance by spending time outdoors—hiking wooded trails, walking through nearby farm fields, and skiing at local mountains. Whether cross-country or downhill, she embraces every season’s chance to be outside.
Family First, Always
- Sara lives close to her family and treasures her role as an active aunt to her spirited young nephew. From everyday moments to extended family reunions—like a recent gathering in Tuscany—she values time spent with loved ones across generations.
A Lifelong Commitment to Movement
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- Staying active is core to Sara’s routine. A devoted follower of the Tracy Anderson Method for nearly a decade, she also makes time for tennis, running, cycling, and yoga—always carving out space in her day to focus on wellness and strength.
Working Remotely, Exploring Globally
- Thanks to the flexibility of remote work, Sara and her husband make the most of their shared love for travel. Whether it’s a weekend in New York or a working stretch abroad, their journeys have recently taken them to Venice, Paris, Grenada, Provence, southern Spain, and Portland, Maine.