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
Skills Required
- 1+ year of experience in sales, business development, recruiting, or similar outreach-heavy role
- Demonstrated experience and results in high-volume cold calling
- Experience conducting outbound outreach via email, phone, and LinkedIn
- 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
- Experience in high-growth environments
What We Do
Heritage Holding is a Boston-based private investment firm targeting lower middle market businesses that generate between two and ten million dollars of EBITDA. The firm partners with founder-led small and medium-sized businesses to support growth, operational improvement, and long-term value creation. It focuses on B2B services across various sectors, including telecom, IT and cybersecurity services, healthcare services, and skilled trades.
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