Senior Director of Revenue Operations

Windward is building the category-defining Maritime AI platform for mission-critical decision-making across government, defense, intelligence, logistics, energy, finance, and global trade. We are looking for a world-class Senior Director of Revenue Operations to help build the operating system that converts that demand into qualified pipeline, accelerates pipeline into bookings, and supports our next stage of growth.

The Senior Director, Revenue Operations will act as a strategic partner to the CRO, owning the systems, analytics, processes, enablement, operating cadence, and performance infrastructure required to help our global GTM organization scale. This is a high-impact leadership role focused on enabling sales teams to exceed quota, helping managers coach and inspect their businesses, improving pipeline quality and forecast accuracy, and driving a globally consistent enterprise sales motion.

This leader will build and run Windward’s GTM operating cadence across forecasting, pipeline reviews, strategic deal reviews, QBRs, territory planning, quota planning, and performance management.

The Senior Director, Rev Ops will work cross-functionally and within Sales to strengthen MEDDPICC discipline, improve account planning, support strategic deal execution, and ensure every manager has the tools and frameworks needed to coach effectively and drive pipeline velocity and success. The role will also own Sales team onboarding and continuous enablement programs that reduce ramp time, improve productivity, and support ongoing learning across the revenue organization.

We are seeking a leader who is AI-forward and excited to build an integrated, modern revenue tech stack. This person will use AI and automation to improve seller productivity, surface deal risks, identify coaching opportunities, strengthen forecasting, accelerate deal progression, and reduce manual work across the GTM organization.

• Build and manage Windward’s global GTM operating cadence, including forecast, pipeline, Q , territory, quota, and strategic deal reviews.
• Create and maintain executive dashboards and analytics for revenue performance, demand conversion, pipeline quality, forecast accuracy, retention, expansion, and seller productivity.
• Equip managers with the tools, scorecards, and frameworks needed to coach teams, improve execution, and accelerate pipeline into bookings.
• Collaborate with Finance, Marketing, Product and Customers groups to ensure alignment in forecasting and execution.
• Sit in Deal Desk and Deal Review meetings to ensure alignment and adherence to company processes.
• Own and optimize the GTM tech stack, including CRM, forecasting, sales engagement, enablement, analytics, and AI-driven workflows.
• Lead sales team’s onboarding and continuous enablement programs that improve ramp time, support enterprise sales execution, and help sellers consistently exceed quota.
• Drive consistent MEDDPICC discipline, stage governance, account planning, pipeline inspection, and strategic deal execution.
• Support the CRO by helping translate strategy into operating priorities, executive communications, and cross-functional execution.
• Help create a globally integrated GTM organization that shares best practices, improves execution consistency, and scales repeatable enterprise sales motions across regions and segments.

This is a unique opportunity to help build the revenue engine behind a category-defining company operating in one of the most important domains in the world. Windward is scaling globally, moving up-market, and expanding across mission-critical government and enterprise use cases. The Senior Director, Revenue Operations will play a central role in making that growth repeatable, measurable, and durable.

• Experience as Senior Rev Ops Director in a Global SaaS company.
• Experience with Sales organizations selling to both the Public Sector and to the Commercial market.