Director, Quote to Cash Systems

About this role

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 ha

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