ABOUT THIS POSITION
The Director, Quote-to-Cash Systems is the system owner and operational leader for Waystar's end-to-end revenue lifecycle within the Information Systems & Infrastructure Operations (IS&IO) organization. This role anchors on Salesforce as the core Q2C system of record while governing a curated hybrid stack of best-of-breed applications — and sits within IS&IO to reflect the enterprise infrastructure ownership, governance accountability, and cross-functional authority required at this level.
The Director leads a team of three direct reports, oversees the Q2C Center of Excellence, and serves as the primary executive escalation point across Revenue Operations, Finance, Sales, and Legal for all quote-to-cash systems matters.
WHAT YOU'LL DO
PLATFORM STRATEGY & ARCHITECTURE
- Define and own the hybrid Q2C architecture: Salesforce as the core system of record + Conga CLM, LinkSquares, Waystar billing platform, Oracle NetSuite, and Planview as integrated best-of-breed applications
- Lead platform evaluation, vendor selection, and rationalization decisions — producing business cases with TCO, NRR impact, and integration risk analysis for SVP and executive review
- Maintain a rolling 18–36 month Q2C systems roadmap aligned to revenue growth, ASC 606 compliance, operational efficiency, and IS&IO infrastructure priorities
- Partner with Data Engineering and IS&IO architecture teams to ensure Snowflake and BigQuery pipelines reflect clean, auditable, ASC 606-aligned Q2C data flows
- Evaluate and assess emerging Q2C technologies, AI-driven automation tools, and integration patterns for relevance to Waystar's hybrid architecture
TEAM LEADERSHIP & COE OPERATIONS
- Lead and develop a team of three direct reports: Sr. CPQ Analyst, Billing Platform Functional Analyst, and PM Tool Administrator
- Establish and operate the Q2C Center of Excellence within IS&IO: governance cadence, RACI, release management, and change control processes
- Set team OKRs tied to quote-to-cash cycle time reduction, quote accuracy rates, billing error rates, and system uptime SLAs
- Develop cross-training and career development plans to eliminate single-point-of-failure risk across the Q2C platform portfolio
- Foster a culture of continuous improvement, operational rigor, and business partnership across the Q2C systems team
PROCESS EXCELLENCE & INTEGRATION
- Drive continuous improvement across the full Q2C lifecycle: Opportunity → Quote → Contract → Order → Billing → Invoice → Revenue Recognition
- Own integration design across all Q2C system boundaries; ensure field-level data fidelity and MuleSoft / Azure Data Factory pipeline health
- Identify and eliminate manual process gaps — specifically bill plan creation failures, lead-to-customer mapping exceptions, and invoice activation lag
- Partner with Finance on ASC 606 revenue recognition configuration and with Legal on contract data governance in LinkSquares
- Define and enforce data standards, field mapping governance, and object model consistency across the Q2C platform portfolio
STAKEHOLDER PARTNERSHIP & GOVERNANCE
- Serve as primary system owner and executive escalation point for Revenue Operations, Finance, Sales, Legal, and the broader IS&IO organization
- Present Q2C performance metrics, roadmap updates, and capital investment proposals to the SVP, IS&IO and cross-functional C-suite stakeholders
- Manage strategic vendor relationships with Salesforce, Conga, Oracle, Planview, and adjacent platform partners
- Represent IS&IO in enterprise architecture reviews and technology governance forums relevant to the Q2C domain
- Maintain and communicate a Q2C systems health dashboard to executive stakeholders on a monthly cadence
WHAT YOU'LL NEED
- 8+ years in Revenue Operations, Sales Operations, or enterprise systems leadership — with 3+ years managing direct reports in an IS/IT or RevOps organization
- Hands-on Salesforce CPQ configuration experience; demonstrated ability to design and govern hybrid Q2C architectures spanning CPQ, CLM, billing, and ERP
- Working knowledge of ASC 606 / IFRS 15 and how revenue recognition requirements drive system design and configuration decisions
- Strong data fluency — able to write and review technical requirements for Snowflake / BigQuery data models supporting Q2C analytics and financial reporting
- Experience reporting to or closely partnering with infrastructure or IS leadership at $500M+ revenue companies
- Demonstrated ability to manage cross-functional stakeholders including Finance, Sales, Legal, and IT in a matrixed enterprise environment
BONUS POINTS
- Salesforce CPQ Administrator or Architect certification
- Conga CLM or DocuSign CLM implementation or administration experience
- Oracle NetSuite ERP integration experience — billing, invoicing, or revenue recognition modules
- Familiarity with MuleSoft or Azure Data Factory for Q2C integration orchestration
- Exposure to Tasktop or comparable project tool integration platforms
- Experience with AI-driven Q2C automation: auto-renewal logic, intelligent pricing, or contract data extraction (e.g., LinkSquares AI)
- Healthcare technology or SaaS recurring revenue business model experience
ABOUT WAYSTAR
Through a smart platform and better experience, Waystar helps providers simplify healthcare payments and yield powerful results throughout the complete revenue cycle.
Waystar’s healthcare payments platform combines innovative, cloud-based technology, robust data, and unparalleled client support to streamline workflows and improve financials so providers can focus on what matters most: their patients and communities. Waystar is trusted by 1M+ providers, 1K+ hospitals and health systems, and is connected to over 5K commercial and Medicaid/Medicare payers. We are deeply committed to living out our organizational values: honesty; kindness; passion; curiosity; fanatical focus; best work, always; making it happen; and joyful, optimistic & fun.
Waystar products have won multiple Best in KLAS® or Category Leader awards since 2010 and earned multiple #1 rankings from Black Book™ surveys since 2012. The Waystar platform supports more than 500,000 providers, 1,000 health systems and hospitals, and 5,000 payers and health plans. For more information, visit waystar.com or follow @Waystar on Twitter.
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.
