Deal Execution Associate at Heritage Holding in Boston, MA

DEAL EXECUTION ASSOCIATE Location: Boston, MA About Heritage Holding Heritage Holding is a Boston-based private investment firm focused on acquiring and operating lower middle market businesses generating $2–10 million of EBITDA. Since 2015, Heritage has completed more than 50 acquisitions across 10+ platforms in B2B services, including telecom, IT and cybersecurity, healthcare services, and skilled trades. We’re not just investors—we’re operators. Our team includes entrepreneurs, former CEOs, and investors passionate about building and running small businesses. Role Overview Heritage Holding is looking to hire one Full-Time Associate to work out of the firm’s Boston office with a Fall 2026 start date. We are looking for a highly driven individual who is a quick learner, shares our passion for acquiring and running businesses, and is ready to take on meaningful responsibility across live deal execution. Roles & Responsibilities The Associate will support the investment team across new platform and add-on acquisition opportunities, including: • Evaluating investment opportunities through market research, business diligence, financial analysis, and assessment of key risks and value creation opportunities • Building financial models, returns analyses, operating forecasts, and transaction scenarios • Preparing investment materials, including deal memos, IOIs, LOIs, and investment committee materials • Managing diligence workstreams across financial, legal, tax, commercial, insurance, and operational diligence • Coordinating with third-party advisors, lenders, legal counsel, accountants, management teams, and business owners throughout transaction processes • Managing data rooms, diligence request lists, Q&A processes, and pre-close deliverables • Supporting negotiation, financing, closing, and post-close handoff processes • Assisting with industry research, market mapping, and evaluation of sourced opportunities Desired Characteristics & Skills • Highly driven, intellectually curious, and detail-oriented • Strong analytical and financial modeling skills • Demonstrated problem-solving ability and sound business judgment • Strong written and verbal communication skills • Ability to manage multiple workstreams in fast-paced transaction processes • Entrepreneurial mindset and willingness to take ownership Desired Qualifications • 3.5 GPA or higher • Demonstrated interest in investing, private equity, M&A, and business ownership • Prior experience in investment banking, private equity, transaction advisory, consulting, corporate development, search funds, or a similarly analytical role preferred • Strong Excel / financial modeling and PowerPoint skills