Deal Origination and Platform Analyst

Heritage Holding•Boston, MA

1d•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. 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 We are hiring a Deal Origination and Platform Analyst Intern to join HH for a two-semester engagement spanning the 2026–2027 academic year. This is not a typical analyst seat. You will split your time across three areas: Direct deal origination — sourcing and qualifying acquisition targets through outbound outreach, intermediary coverage, and industry research. Origination infrastructure — maintaining and improving the tooling, data, and workflows (CRM, sourcing automations, lead enrichment, dashboards) that power our pipeline. Portfolio company GTM support — working alongside operators at HH portfolio companies on go-to-market execution: outbound campaigns, sales tooling, lead generation, and revenue operations. The role suits someone who is equally comfortable picking up the phone, building a financial model, writing a SQL query, and standing up a Clay workflow. You should be 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 — not just an interest in finance.
Comfort with cold outreach and talking to business owners. You don’t have to love it on day one, but you have to be willing to learn fast.
Technical fluency: you can build a clean Excel model AND you’re the kind of person who would write a Python script or set up a Clay table to avoid doing something manually twice.
High ownership, low ego, fast learner.
Comfortable navigating ambiguity in a small team.
Strong written and verbal communication — a meaningful share of the job is written outreach and internal memos.

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 — cold calls, emails, LinkedIn, and intermediary coverage.
Run thesis-driven sourcing sprints in target industries (IT services, healthcare services, business services); produce 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 — financial summaries, EBITDA bridge work, 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: HubSpot CRM hygiene, contact enrichment, deal stage discipline, and reporting.
Build and improve sourcing automations using tools like Clay, Apollo, SourceScrub, and Smartlead — from list-building to outreach sequencing to reply handling.
Design dashboards and reports that give the partners real-time visibility into pipeline coverage, broker activity, and deal velocity.
Identify and prototype new tools or workflows (including LLM-assisted tooling) that meaningfully reduce manual work or improve sourcing yield.
Document playbooks so that improvements outlast any single intern cohort.
Embed with one or more HH portfolio companies on time-bound GTM projects — e.g., 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 (Clay, Apollo, Smartlead, HubSpot, etc.).
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 that can be deployed across the portfolio.