Sales Development Representative

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.

About the Role

Heritage Holding is seeking a driven and entrepreneurial Sales Development Representative to join our Deal Sourcing team. In this role, you’ll be responsible for identifying and engaging potential opportunities, building relationships with business owners and stakeholders, and helping drive the firm’s pipeline of prospective investments. This is a high-impact position with visibility across the organization, offering the chance to shape sourcing strategy and contribute directly to the firm’s growth.

What You’ll Do

• Identify, research, and engage potential acquisition or investment opportunities aligned with Heritage Holding’s criteria

• Conduct outbound outreach via email, phone, and LinkedIn to connect with business owners, operators, and intermediaries

• Qualify opportunities through thoughtful discovery conversations to understand business fundamentals, goals, and fit

• Schedule and support introductory meetings between prospective opportunities and internal stakeholders

• Own and refine sourcing strategies, including target lists, messaging, and outreach channels

• Partner with internal teams to provide feedback on market trends, outreach effectiveness, and opportunity quality

• Maintain organized and up-to-date pipeline tracking and reporting

• Contribute to achieving team sourcing and deal pipeline targets

What You Bring

• 1+ year of experience in sales, business development, recruiting, or a similar outreach-heavy role (experience in high-growth environments is a plus)

• Demonstrated experience, interest and results in high-volume cold calling is highly preferred

• Strong communication skills with the ability to build trust quickly and engage a range of stakeholders

• High emotional intelligence and ability to navigate nuanced conversations with business owners

• Motivation to be part of a team focused on sourcing and evaluating new opportunities