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.

WHAT YOU'LL DO

• 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

WHAT YOU'LL NEED

• 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, or Strategy, including 5+ years leading large, cross‑functional transformation initiatives
• You have a proven ability to lead and execute enterprise‑wide projects, driving alignment and measurable outcomes across diverse teams
• You thrive in a fast‑paced, highly collaborative environment and are known for rolling up your sleeves to get things done
• You have deep expertise in QTC processes, including contracting, pricing, CPQ, billing, invoicing, and revenue recognition
• You have working knowledge of CRM systems (ideally Salesforce) and understand how they integrate into broader operational workflows
• You are an effective change leader, capable of influencing senior stakeholders, building alignment, and driving adoption without direct authority
• You have significant experience partnering with Engineering, Product, and Data teams to design and implement scalable solutions
• You are an exceptional communicator, with strong verbal and written skills and proficiency in Microsoft Office and PowerPoint
• You possess strong presentation and storytelling skills, with the ability to translate complexity into clear, persuasive narratives
• You are highly detail‑oriented, quick to learn new concepts, and comfortable navigating evolving business models and technologies
• You are organized, efficient, and able to prioritize and execute multiple initiatives simultaneously

BONUS POINTS

• You have a master’s degree in business, operations, or technology disciplines
• You have experience in healthcare technology, SaaS, or high-volume multi-product organizations
• You have experience consulting on Enterprise level QTC implementations

WAYSTAR PERKS

• Competitive total rewards (base salary + bonus, if applicable)
• Customizable benefits package (3 medical plans with Health Saving Account company match)
• We offer generous paid time off for our non-exempt team members, starting with 3 weeks + 13 paid holidays, including 2 personal floating holidays. We also offer flexible time off for our exempt team members + 13 paid holidays
• Paid parental leave (including maternity + paternity leave)
• Education assistance opportunities and free LinkedIn Learning access
• Free mental health and family planning programs, including adoption assistance and fertility support
• 401(K) program with company match
• Pet insurance
• Employee resource groups

Waystar is proud to be an equal opportunity workplace. We celebrate, value, and support diversity and inclusion. Qualified applicants will receive consideration for employment without regard to race, color, religion, age, sex, national origin, disability status, genetics, marital status, protected veteran status, sexual orientation, gender identity or expression, or any other characteristic protected by federal, state, or local laws.

This applies to all terms and conditions of employment, including recruiting, hiring, placement, promotion, termination, layoff, recall, transfer, leaves of absence, compensation, and training.