GTM Operations Lead at Heritage Holding

About Heritage Holding

Heritage Holding is a Boston- and NYC-based small business investment firm targeting founder and family owned small businesses that generate between $5m and $50m dollars of revenue. Alex de Pfyffer and Ross Porter founded Heritage as a Search Fund after graduating from Harvard Business School in 2015. Heritage closed a $220m first institutional fundraise in August of 2024 and has completed +60 acquisitions across 12 platform companies in B2B services, including telecom, IT and cybersecurity services, healthcare services, and skilled trades services (HVAC, Electrical, Fencing, Engineering).

We were operators before investors. Our team is composed of entrepreneurs, former CEOs, and investors who are passionate about operating small businesses.

Our portfolio companies generate almost half a billion dollars in revenue. Growth is where we earn our returns. We invest in good businesses run by founders who built them on reputation and referrals, and we help them add a real go-to-market engine: targeting, outbound, marketing, a CRM the team actually uses, and the reporting to know what is working. Our growth team embeds in the portfolio companies to make that happen, and this role is at the center of it.

Role Overview

Heritage Holding is hiring a GTM Operations Lead to lead go-to-market system implementations across our portfolio companies.

Our companies sell to commercial customers in IT services, healthcare services, and the trades. Some have a sales team and CRM in place at acquisition, other times we’re starting from a blank slate. You will help assess each company’s GTM at acquisition, standardize measurement using our proprietary methodologies, roll out GTM systems within each business, hire full-time dedicated GTM Engineers in each platform, and keep improving our efforts as results come in.

The ultimate goal with this role is to take our GTM methodologies, make them work reliably inside each portfolio company, then help propagate what works from one business to the next.

You will report to Sam Kramer, who leads sourcing and growth, and work directly with Heritage’s founding partners, advisory team, and portfolio company executives.

Key Responsibilities

• Implement Heritage’s proprietary GTM measurement, attribution, and productivity methodologies across portfolio companies, including the financial modeling required to connect marketing and sales activity to pipeline, revenue, and customer economics.

• Stand up and maintain the foundational GTM systems required to support those methodologies, generally using HubSpot as the system of record. This includes CRM architecture, data models, pipelines, custom properties, forms, workflows, integrations, attribution, and executive reporting.