Deal Origination and Platform Analyst

Heritage Holding•Boston, MA

3d•$15 - $20•Onsite

About The Position

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. The firm is looking for a Deal Origination and Platform Analyst Intern for a two-semester engagement spanning the 2026–2027 academic year. This role involves direct deal origination through outbound outreach, intermediary coverage, and industry research; maintaining and improving origination infrastructure like CRM, sourcing automations, and dashboards; and supporting portfolio company go-to-market execution. The ideal candidate is comfortable with a mix of outreach, financial modeling, SQL, and workflow automation, and is excited about the intersection of investing, operations, and technology.

Requirements

Currently enrolled in an undergraduate or graduate program; all majors considered.
Strong academic record.
Genuine interest in private equity, entrepreneurship through acquisition (ETA), and operating roles.
Comfort with cold outreach and talking to business owners.
Technical fluency: ability to build a clean Excel model and willingness to use scripting (e.g., Python) or tools (e.g., Clay) to automate tasks.
High ownership, low ego, fast learner.
Comfortable navigating ambiguity in a small team.
Strong written and verbal communication skills.

Nice To Haves

Prior exposure to HubSpot (or another CRM), SQL, Python, Clay, Apollo, SourceScrub, Smartlead, or similar B2B GTM tooling.

Responsibilities

Develop and manage a pipeline of qualified deal leads through proactive outbound activities such as cold calls, emails, LinkedIn, and intermediary coverage.
Run thesis-driven sourcing sprints in target industries (IT services, healthcare services, business services), producing target lists, market maps, and outreach strategies.
Build and maintain relationships with business owners, founders, brokers, and investment bankers.
Conduct preliminary diligence on inbound CIMs and teasers, including financial summaries, EBITDA bridge work, and fit screens, and surface live opportunities to the deal team.
Build financial models for submission to the investor committee.
Track and report on pipeline activity, conversion metrics, and outreach effectiveness.
Own the day-to-day health of the HH origination stack, including HubSpot CRM hygiene, contact enrichment, deal stage discipline, and reporting.
Build and improve sourcing automations using tools like Clay, Apollo, SourceScrub, and Smartlead, covering list-building, outreach sequencing, and reply handling.
Design dashboards and reports to provide partners with real-time visibility into pipeline coverage, broker activity, and deal velocity.
Identify and prototype new tools or workflows (including LLM-assisted tooling) to reduce manual work or improve sourcing yield.
Document playbooks to ensure improvements persist beyond a single intern cohort.
Embed with one or more HH portfolio companies on time-bound GTM projects, such as outbound campaign builds, ICP refinement, lead-gen experiments, CRM cleanups, sales rep enablement, or pricing tests.
Translate origination-side tooling and best practices into portfolio operating value using tools like Clay, Apollo, Smartlead, and HubSpot.
Partner with portco operators and HH’s value-creation team to scope projects, set KPIs, and report results back to the HH investment team.
Build reusable GTM templates and playbooks for deployment across the portfolio.