# Head of GTM Systems and Engineering

**Company:** [Applecart](https://hotfix.jobs/companies/applecart)
**Location:** New York, NY
**Role:** GTM Engineering
**Salary:** $200k – $230k/yr
**Experience:** 8+ years
**Skills:** Salesforce, HubSpot, Make, n8n, Zapier, OpenAI API, Claude API, Gemini Api, Reverse Etl, Data Pipelines, Llm Integration, Gtm Orchestration
**Posted:** 2026-04-28

> Lead architect of the Revenue Operating System, designing GTM automation, data pipelines, and AI-powered workflows connecting Marketing, Sales, and Success. Requires 8+ years in technical RevOps/GTM Engineering with expert Salesforce and HubSpot skills.

## Job Description

## What You’ll Do

**Orchestration Layer**: Design the high-level architecture that connects our core GTM tech stack. Own the State Machine of our revenue engine, defining exactly how data moves, changes, and triggers actions across our GTM stack.

**Stack Consolidation & Modernization**: Evaluate our existing tools through a performance-first lens.

**Advanced Lifecycle Orchestration**: Architect the technical workflows that govern the entire customer journey, including complex round-robin routing and post-sales transition protocols.

**Data Pipeline Ownership**: Engineer the flow of GTM data from our CRM and engagement tools into the reporting layer. Ensure that every required field is automatically populated, formatted, and validated.

**LLM-Powered Data Synthesis**: Engineer automated pipelines that use LLMs to transform unstructured data (Gong transcripts, email threads, LinkedIn signals) into high-fidelity, structured CRM data. Move the organization away from manual data entry toward a Zero-Entry CRM environment.

**Agentic Workflow Design**: 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.

**AI Stack Integration**: Evaluate and implement the next generation of AI-native GTM tools and integrate them into the core GTM architecture.

**Sandbox & Deployment**: Implement a rigorous deployment process. No logic goes live without being tested in a sandbox to ensure zero disruption to GTM.

**Systems Documentation**: Maintain a technical Schema Map of our entire GTM engine so the organization understands the logic behind every automation.

**Error Handling & Resilience**: Treat GTM systems like production software. Build monitoring and self-healing automations that alert the team when data syncs fail or logic breaks.

## Experiences and Capabilities You Bring

- The Architect Mindset: See tools as logic gates, data schemas, and API endpoints. A systems thinker who builds for the 10x version of the company.
- CRM Dual-Mastery: Expert-level technical knowledge of both Salesforce (Flow, Architecture) and HubSpot (Advanced Workflows, Custom Objects). Understand friction points between these platforms and how to solve them.
- 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.
- Architect and maintain high-performance Data Activation (Reverse ETL) pipelines that bridge the gap between our Data Warehouse and the GTM stack. Ensure that models built in the warehouse are pushed into CRM as actionable signals, not just static fields.
- 8+ years in a technical RevOps or GTM Engineering role, preferably within a high-velocity B2B environment.

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**Apply:** https://hotfix.jobs/jobs/3c7ab426-b091-470f-be3e-2127dcc11fe5
**Canonical:** https://hotfix.jobs/jobs/3c7ab426-b091-470f-be3e-2127dcc11fe5