Head of GTM Systems and Engineering

Applecart; New York (NY); Hybrid; USD 200,000 - 230,000; Full time

Job summary

Applecart, a leading technology company in New York City, is seeking a Head of GTM Systems and Engineering to lead the architecture of our Revenue Operating System. The role focuses on automating processes that connect Marketing, Sales, and Success, ensuring every opportunity is managed efficiently. Ideally, candidates should have 8+ years of experience, expert knowledge of Salesforce and HubSpot, and proficiency with LLM APIs. This hybrid role offers a competitive salary of between $200,000 and $230,000, plus equity compensation, based on experience.

Qualifications

• 8+ years in a technical RevOps or GTM Engineering role, preferably in high-velocity B2B.
• Expert-level technical knowledge of Salesforce and HubSpot, knowing integration friction points.
• Experience building workflows with LLM APIs to automate cognitive tasks.

Responsibilities

• Design high-level architecture that connects core GTM tech stack.
• Evaluate existing tools for performance improvement.
• Architect technical workflows governing customer journey.

Skills

Architect Mindset

CRM Dual-Mastery

Expertise in orchestration platforms

Proficiency in LLM APIs

Data Activation pipelines

8+ years in RevOps or GTM Engineering

Tools

Salesforce

HubSpot

Make

n8n

Zapier

Job description

About Us

Applecart is the leading technology company that C-suites rely on to reach business‑critical decision makers. The most important decisions are made by the hardest people to reach and influence. Historically, C‑suite leaders have lacked the tools to reach the stakeholders who matter most to their business. The C‑suites of hundreds of Fortune 500 companies, major agencies, trade associations, nonprofits and governments use Applecart to put their best content in front of business‑critical decision makers and those they trust — from policymakers and investors to CEOs, key employees, members of the media and more. Decision makers are informed by what they read, learn from advisors, hear from colleagues and discuss with family and friends. To break through to them, you must reach them through the only channel that really moves them: those they know and trust. Applecart’s platform uses publicly available data to map billions of social relationships between nearly every American adult and enable clients to deliver content directly to decision makers and those who matter most to them.

We are hiring a Head of GTM Systems and Engineering in our New York City office.

About The Role

The Head of GTM Systems & Engineering is the lead architect of our Revenue Operating System. Your goal is to move the organization away from manual, disconnected processes and toward a fully automated, logic‑driven GTM machine. You 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 will be a high‑impact role, helping drive profitable revenue growth.

What You’ll Do

• Orchestration Layer: Design the high‑level architecture that connects our core GTM tech stack. You 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. This includes 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. You 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. You will 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. You will 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: You don’t see tools; you see logic gates, data schemas and API endpoints. You are 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). You know exactly where the friction points are between these two 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. You will ensure that models built in the warehouse are pushed into CRM as actionable signals, not just static fields.
• Experience: 8+ years in a technical RevOps or GTM Engineering role, preferably within a high‑velocity B2B environment.

This is a hybrid role. Work from home on Monday and Friday and in Applecart’s New York City office Tuesday through Thursday.

Compensation

Our compensation package consists of three components: (i) a base salary, (ii) bonus / variable compensation and (iii) generous equity compensation. The base salary range for this role is between $200,000 and $230,000, based on the candidate’s experience and skills relative to the requirements listed in the “Who You Are” section above. The bonus / variable compensation is based on individual, team and company performance. The salary range excludes additional compensation that candidates will receive in the form of equity. The range applies to candidates located in the New York City area.

A Few Facts About Us

• Applecart’s platform has been used by hundreds of industry‑leading clients spanning Fortune 500 companies such as Blackstone and Intuit, leading nonprofit organizations such as the Environmental Defense Fund, and top‑tier advertising and communications agencies such as Teneo, FGS, Weber Shandwick and OMD.
• Applecart is growing quickly — over the last 4 years, we’ve increased our revenue by 10X, grown our headcount by almost 5X and are cash‑flow positive.
• The senior leadership team includes two members of the Forbes 30 under 30 list for Marketing and Advertising, the former Head of Product at Moat, Oracle’s online ad measurement platform, a former senior White House advisor, early sales and talent leaders from Google and Twitter, two of the Democratic Party’s most successful pollsters and strategists, and alums of top‑tier organizations such as Bain & Company, Amazon and Simpson Thacher.
• Applecart raised a $100M Series C from Blackstone’s tech growth fund at the end of 2025. Other investors include Bain & Company, global sports, entertainment and marketing giant Endeavor, KKR Co‑Founder Henry Kravis, entrepreneur Chris Burch, a founder of Palantir, senior engineering leaders at Twitter and Yelp, former Fortune 50 and advertising agency CEOs and a number of well‑known venture capitalists. Ari Emanuel, CEO of TKO and Executive Chairman of WME, Wayne Berman, Blackstone’s Head of Global Government Affairs, and Risa Heller, CEO of HELLER, serve on our board.
• Our work has been featured on Morning Joe on MSNBC, BloombergTV, The Colbert Report, Axios, Semafor, BusinessWeek, the Associated Press, Forbes, the Washington Post and Politico among many others.