Head of GTM Systems and Engineering

Applecart•New York, NY

4h•Hybrid

About The Position

The Head of GTM Systems & Engineering is the lead architect of Applecart's Revenue Operating System. This role is responsible for transitioning the organization from manual, disconnected processes to a fully automated, logic-driven Go-To-Market (GTM) machine. The individual will own the technical plumbing and orchestration layer that connects Marketing, Sales, and Success, ensuring that every lead, account, and opportunity moves through a perfectly engineered lifecycle. Reporting to the SVP, Revenue Operations, this is a high-impact role aimed at driving profitable revenue growth.

Requirements

Possess an Architect Mindset, seeing tools as logic gates, data schemas, and API endpoints, and building for the 10x version of the company.
Demonstrate CRM Dual-Mastery with expert-level technical knowledge of both Salesforce (Flow, Architecture) and HubSpot (Advanced Workflows, Custom Objects), including understanding and solving friction points between these platforms.
Expert proficiency in Make, n8n, Zapier, or similar enterprise-grade orchestration platforms.
Proven experience building workflows that call LLM APIs (OpenAI, Anthropic, or Gemini) to automate complex cognitive tasks.
Ability to architect and maintain high-performance Data Activation (Reverse ETL) pipelines that bridge the gap between our Data Warehouse and the GTM stack, ensuring models built in the warehouse are pushed into CRM as actionable signals.
8+ years in a technical RevOps or GTM Engineering role, preferably within a high-velocity B2B environment.

Responsibilities

Design the high-level architecture that connects our core GTM tech stack, owning the State Machine of our revenue engine, defining exactly how data moves, changes, and triggers actions across our GTM stack.
Evaluate our existing tools through a performance first lens for Stack Consolidation & Modernization.
Architect the technical workflows that govern the entire customer journey, including complex round-robin routing, and post sales transition protocols.
Engineer the flow of GTM data from our CRM and engagement tools into the reporting layer, ensuring that every field required is automatically populated, formatted, and validated.
Engineer automated pipelines that use LLMs to transform unstructured data (Gong transcripts, email threads, LinkedIn signals) into high-fidelity, structured CRM data, moving the organization away from manual data entry toward a Zero-Entry CRM environment.
Architect Agentic loops where AI agents perform autonomous GTM tasks such as automated account research, lead qualification based on custom ICP logic, and Next Best Action recommendations.
Evaluate and implement the next generation of AI-native GTM tools and integrate them into the core GTM architecture.
Implement a rigorous deployment process, ensuring no logic goes live without being tested in a sandbox to ensure zero disruption to GTM.
Maintain a technical Schema Map of our entire GTM engine so the organization understands the logic behind every automation.
Build monitoring and self-healing automations that alert the team when data syncs fail or logic breaks, treating GTM systems like production software.