Director, Quote to Cash Systems

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.

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

• 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

• 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

• 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