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 $155,000-205,000 based on skill set and experience
What Do We Offer?
Interesting Work | We hire curious trendspotters and brave trendsetters. This is NOT your boring, routine, cushy, rest-and-vest corporate job. This is the “challenge yourself” role where you learn something new every day, never stop growing, and have fun while you’re doing it.
Tribe Vibe | We are more than colleagues, we are a tribe. We have a strict “no a**hole policy” and enforce it diligently. This means we spend time together - with spontaneous office happy hours, organized outings, and community volunteer opportunities. We are a diverse and distributed team, but we like to stay connected.
Bragging Rights | We are dreamers and dream makers. Our efforts pay off and we work with the most prestigious brands, from big-name retailers to airlines, to professional sports teams. Your contribution will make an impact with many of the most recognizable names in almost every industry including AirFrance KLM, ASICS, Burberry, Mattel, Mitsubishi, Walmart, and many more!
One Team One Dream | This is one of our values, and it shows. We don’t believe in artificial hierarchies. If you’re part of the tribe, you have an opportunity to contribute. Your voice will be heard and you will also receive regular updates about the business and its performance. Which, btw, is through the roof, so it’s a great time to be joining…
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