Revenue Operations Leader, Strategy & Planning

What Are We Looking For?

Contentstack is a growth-stage enterprise SaaS company with an ambitious goal of reaching $250M ARR. Getting there means rethinking how we operate and scale our go-to-market (GTM) organization - not simply increasing costs as revenue grows.

To support this vision, we recently established our GTM Strategy & Systems (GSS) team under the Office of the CEO. This team brings strategy, systems, and execution together under one leader, connecting Revenue Operations, Analytics, GTM Applications, and a newly formed GTM Engineering capability.

We’re looking for a Revenue Operations Leader, Strategy & Planning to build the planning and performance-management foundation that powers this organization. You’ll work closely with the CRO, Finance, and GTM leaders to turn business objectives into actionable plans, establish a clear view of performance, and help the business identify and address opportunities and risks early.

This is a hands-on builder role for someone who enjoys creating structure, challenging assumptions, and turning complex data into decisions that drive growth. If you're excited to help shape how a scaling enterprise SaaS company operates, we'd love to hear from you! Here’s what you’ll be doing:

• Lead GTM planning: Own annual planning across capacity, territories, quotas, and incentive-plan design. Build scenario models that clearly communicate tradeoffs, dependencies, and assumptions to GTM and Finance leadership.
• Drive performance management: Establish a rigorous forecasting approach and evaluate performance against the plan across pipeline, productivity, bookings, retention, and expansion. Identify gaps and partner with GTM leaders to determine what needs to change.
• Turn insights into action: Translate performance trends into clear recommendations, helping leadership understand risks, identify opportunities, and make informed decisions.
• Establish measurement and governance: Define and maintain cross-functional KPIs that ensure Finance, Sales, Marketing, and Customer Success are working from consistent metrics and business definitions.
• Improve cross-functional alignment: Identify gaps in reporting, measurement, and assumptions, and work with stakeholders to resolve issues and document agreed-upon standards.
• Leverage AI and automation: Build agent-enabled workflows that streamline recurring analysis, surface meaningful changes, and make business insights easier to access.

What Really Gets Us Excited About You?

• 8–15+ years of experience in Revenue Operations, Sales Strategy, GTM Finance, or a similarly analytical role within a B2B SaaS organization.
• Direct ownership of annual GTM planning across capacity, territories, quotas, and compensation design, with the ability to confidently defend planning assumptions with CRO and CFO-level stakeholders.
• Strong command of forecasting, funnel economics, and SaaS growth metrics, with the hands-on ability to analyze complex pipeline, bookings, and customer data.
• Experience with demand-generation metrics and the Marketing-to-Sales handoff, including funnel-stage definitions, conversion rates, and lead routing.
• Hands-on experience building or significantly shaping segmentation, scoring, or attribution models, with the ability to assess the reliability of inputs and effectiveness of outputs.
• Experience building and deploying AI or agentic workflows that expand analytical capacity, streamline recurring analysis, or improve business decision-making.
• You’re a high-agency builder who enjoys creating new capabilities, raising standards, and rethinking processes as the business evolves.
• You build trust across functions and are comfortable challenging assumptions with senior leaders when the data tells a different story.
• You know when a directional answer is enough to move forward, when precision matters, and how to communicate uncertainty.
• You stay close to the details while keeping broader business objectives in view, and know when to gather input versus when to take ownership and move forward.
• You’ve built trusted partnerships with CROs and GTM leaders and know how to influence decisions while plans are still taking shape.
• You value a collaborative, innovative, and fun culture!

Salary for this role ranges between $155,000-195,000 based on skill set and experience