What Are We Looking For?

We are seeking an experienced and strategic VP, GTM Strategy & Systems to own Contentstack’s AI-native go-to-market operating system end to end. Reporting directly to the CEO, this role will partner closely with the CRO, CMO, and CFO to translate growth strategy into the data, systems, workflows, and AI-augmented processes that power our go-to-market organization.

This is a senior executive leadership role with ownership across three pillars: GTM Ops & Analytics, GTM Engineering, and GTM Apps. You’ll be responsible for building the infrastructure that allows our GTM organization to scale more efficiently, improve decision-making, and leverage AI without simply adding headcount.

Contentstack is an AI-forward company, and we believe foundation comes before automation. You’ll help establish the clean data, documented processes, clear ownership, and governance required to move our GTM organization from humans doing the work, to humans overseeing AI-powered systems that can operate at scale.

If you’re excited about building an AI-native GTM operating system and shaping how a growing enterprise SaaS company scales from ~$100M to $250M ARR, we’d love to hear from you! Here’s what you’ll be doing:

• Own the GTM operating system across GTM Ops & Analytics, GTM Engineering, and GTM Apps, ensuring our people, processes, data, and technology work together as one system.
• Lead revenue, marketing, and partner operations, including pipeline, forecasting, territory and quota planning, deal desk, renewals, services, funnel operations, lead routing, attribution, partner pipeline, and GTM performance reporting.
• Build and evolve our GTM architecture, including process design, operating cadence, web and GTM infrastructure, and the AI/agent layer that runs across it.
• Own the GTM technology ecosystem, including Salesforce, CPQ, marketing automation, integrations, APIs, MCP surfaces, permissions, and governance, ensuring our systems function as a coherent platform rather than disconnected tools.
• Partner with AI and Engineering to identify, prioritize, and deploy high-impact agent and workflow automation use cases across the revenue funnel.
• Build and lead the GTM Systems organization, including pillar leads and teams across architecture/engineering, applications, and operations/analytics, while establishing clear governance and accountability across functions.
• Establish the GTM data foundation and operating cadence, creating shared definitions, clean data, trusted reporting, and a consistent rhythm for pipeline, forecasting, and business reviews.
• Drive measurable GTM efficiency, using AI, automation, and better systems to increase organizational capacity without scaling headcount in lockstep with revenue.

What Really Gets Us Excited About You?

• 12+ years of experience across GTM functions within enterprise SaaS, including experience navigating hypergrowth, transformation, and scaling operating discipline.
• Proven experience building and owning GTM systems, data architecture, and operating infrastructure, rather than simply consuming reports or managing an inherited process.
• Hands-on AI and automation experience in a GTM environment, including deploying agents or automated workflows and understanding governance, permissions, auditability, and data quality.
• Deep expertise in the modern GTM technology stack, particularly Salesforce and its ecosystem, along with pipeline management, forecasting, revenue operations, and GTM analytics.
• Experience building teams and operating capabilities from the ground up, including diagnosing gaps, defining the architecture, and making thoughtful hiring and investment decisions.
• Strong ability to operate as both a hands-on builder and executive strategist, moving comfortably from stakeholder interviews and process diagnostics to architecture, prioritization, and organizational decisions.
• Exceptional executive presence and cross-functional influence, with the ability to drive adoption, establish governance, and create alignment across Sales, Marketing, Customer Success, Services, Partnerships, Product, Engineering, Finance, and the CEO’s Office.
• You’re comfortable making clear trade-offs and setting boundaries, knowing what belongs within GTM Systems and where ownership should remain with other functions.
• You like occasional travel.
• You value a collaborative, innovative, and fun culture and are excited about helping define what an AI-native go-to-market organization can look like in practice.

Salary for this role ranges between $275,000-300,000 based on skill set and experience