GTM AI Engineering Lead

GTM AI Engineering 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 AI Engineering 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.

• Implement and support inbound and outbound pipeline-generation systems, including targeting, list building and enrichment, sequencing, copy, deliverability, website conversion, email, events, referral programs, and paid media tracking.

• Ensure GTM activity can be tied back to revenue with reporting that portfolio company leadership and Heritage partners can trust.

• Document and memorialize the GTM playbooks, workflows, system configurations, and operating processes implemented within each company so they can be maintained and replicated.

• Work closely with Heritage’s operations leaders and portfolio company executives to roll out new GTM systems, drive adoption, troubleshoot issues, and improve execution over time.

• Help hire, onboard, and support dedicated GTM Engineers within portfolio companies who can take ongoing ownership of the systems and workflows implemented by Heritage.

• Propagate proven practices, workflows, automations, and system configurations from one portfolio company to the next.

• Standardize GTM metrics and reporting across the portfolio so Heritage can evaluate performance consistently across companies and identify areas that require attention.

• Implement AI agents, automations, and internal tools that reduce or eliminate manual work across sales and marketing processes.

• Build and maintain AI-enabled, multi-user workflows that allow small sales and marketing teams to operate with substantially greater productivity.

• Maintain a working knowledge of emerging GTM tools, AI capabilities, and automation technologies; test and implement the ones that are useful within Heritage’s existing GTM framework.

Qualifications

• At least 5 years of experience in GTM engineering, growth, RevOps, sales operations, marketing operations, or a similarly hands-on commercial systems role.

• Deep, hands-on experience with HubSpot in production environments, including custom properties, workflows, reporting, integrations, data hygiene, and CRM administration.

• Experience building attribution and performance reporting across multiple acquisition channels, including major ad platforms such as Google and Meta, and tying activity back to pipeline, revenue, CAC, and ROAS.

• Experience supporting both inbound and outbound growth motions, including targeting, enrichment, sequencing, deliverability, lead routing, conversion tracking, and lifecycle management.

• Strong working knowledge of modern GTM tooling such as Clay, Zapier, Make, Dripify/HeyReach, enrichment providers, call-tracking platforms, and related sales and marketing infrastructure.

• Real experience using LLMs, AI agents, and automation in operational workflows. We are less interested in using AI to draft emails or summarize meetings and more interested in systems that materially improve productivity or eliminate manual work.

• Strong systems thinking and comfort working with complex, imperfect data. You should understand how data needs to be structured before building reports, workflows, or automations on top of it.

• Working knowledge of APIs, webhooks, JSON, and data integrations. Experience with SQL, Python, or similar tools is strongly preferred.

• Ability to move comfortably between strategy and implementation: understand the operating model, translate it into working systems, and troubleshoot when reality does not match the design.

• Experience in high-growth startups, founder-led businesses, small businesses, or other resource-constrained operating environments is strongly preferred. Private equity experience is helpful but not required.

• Strong analytical and financial instincts, with the ability to understand how GTM activity translates into revenue, margin, customer economics, and business performance.

• High EQ, high integrity, low ego, and a strong bias for action. You should be comfortable working directly with founders, executives, sales teams, marketers, and operators, and willing to get into the details when needed.