ABOUT THIS POSITIONThe 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 DOPLATFORM 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
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
