Director, Quote to Cash Operations + Strategy

ABOUT THIS POSITION

We’re looking for a Director of Quote‑to‑Cash Operations and Strategy to serve as a strategic partner to Waystar Finance leadership, owning the end‑to‑end health, performance, and evolution of our revenue lifecycle. In this role, you’ll lead ongoing modernization of our core business and financial processes, redesigning complex workflows, strengthening data pipelines, and implementing scalable, automated solutions that enhance billing accuracy, improve operational efficiency, and support long‑term business growth.

You will take continuous ownership of the Quote‑to‑Cash ecosystem, translating fragmented, manual, or highly technical processes into streamlined, automated, and insight‑driven operational capabilities. You’ll work closely with teams across Sales, Legal, Finance, Product, Engineering, and Implementation to identify bottlenecks, evaluate process effectiveness, and champion improvements that elevate consistency, accuracy, and cross‑functional alignment.

The ideal candidate brings deep experience leading enterprise‑wide operational programs, with exceptional critical‑thinking, communication, and change‑leadership skills. You’ll provide a proactive, consultative voice across the organization; clarifying priorities, influencing senior stakeholders, and shaping strategic decisions that strengthen Waystar’s revenue operations foundation for years to come.

• Serve as the accountable leader for the enterprise‑wide Quote‑to‑Cash (QTC) transformation, defining the strategy, scope, success metrics, and phased delivery roadmap
• Translate strategic business objectives into actionable operational plans, including process optimization, data‑flow redesign, automation enablement, and systems alignment
• Conduct deep performance analyses across key indicators, such as engagement, retention, throughput, and conversion; to support both internal operational teams and customer‑facing functions
• Own all governance and communication routines, including steering committee updates, progress reporting, and executive‑level insights
• Lead a comprehensive assessment and redesign of QTC processes spanning quoting, pricing approvals, contracting, project creation, implementation, bill‑plan setup, invoicing, and revenue recognition
• Identify manual touchpoints, data‑entry risks, and workflow bottlenecks, designing scalable, standardized solutions that reduce operational lift and lessen dependencies on Engineering
• Develop and maintain standardized documentation, including process maps, operating procedures, and cross‑functional workflow guides
• Partner with Engineering and Data teams to architect improved data‑flow models for contract data, transaction volumes, billing triggers, and revenue feeds
• Guide enhancements across core systems, including CPQ, CRM, contract repositories, billing platforms, and automation tools
• Ensure seamless and audit‑ready integration across functional handoffs from Sales → Legal → Implementation → Finance
• Drive initiatives that accelerate billing start dates, including minimum‑usage validation, automated billing triggers, and reduced reliance on first‑transaction events.
• Provide visibility into accounts approaching billing thresholds, minimizing manual review and ensuring proactive operational action
• Lead organizational change management, including stakeholder communication, training, adoption planning, and ongoing reinforcement
• Champion the value of QTC modernization, creating clarity and excitement around how improvements accelerate revenue, enhance speed‑to‑market, and strengthen operational scalability
• Build and lead a high‑performing QTC transformation team, including project managers, analysts, and cross‑functional subject‑matter experts
• Foster a culture of accountability, data‑driven decision‑making, and continuous improvement across all QTC initiatives

• You live our values, bringing a positive attitude, professionalism, and respect for others in every interaction
• You hold a bachelor’s degree in business, operations, technology, or a related discipline.
• You bring 10+ years of experience across Revenue Operations, Sales Operations, Finance, Business Operations,…