Order to Cash Lead

Responsibilities

Strategy & policy

• Own the end-to-end Order to Cash process with a growth mindset. Proactively identify gaps, generate creative solutions, and roll up your sleeves to fix issues while thinking strategically about long-term process health and scalability.
• Maintain standard invoicing and payments term framework. Review non-standard requests in incoming contracts and partner with Sales on a defined exception path
• Regularly optimize credit policy: decisions on which customers go on invoicing vs. pay-by-bank/credit card, credit-limit setting, and the hold policy
• Partner with the CFO on the cash-flow and financing implications of AR aging, including the company’s line of credit, borrowing base, and DSO trajectory

Operations & execution

• Manage WorkWhile’s outsourced AR and collections team - set the operating cadence, metrics, and customer prioritization
• Drive the open backlog; partner with AEs and AMs on aged AR; bring customer-specific issues to resolution
• Enforce customer holds when warranted. Run the weekly AR/AM/Finance process and AR Analysis where holds are decided
• Own VMS customer invoice reconciliation end-to-end. Partner with Operations on root-cause resolution, manage credit and payment allocation reconciliation, ensure WorkWhile invoice / customer VMS invoice / QBO financials tie out, and drive Engineering to build automation and API connections between systems.
• Represent Finance externally on new customer invoice requirements and requests; own customer escalations on disputes and issues.
• Serve as Finance Admin for WorkWhile internal Admin Portal for policy configurations that impact Customer Invoicing

Product & Roadmap

• Leverage modern AI-native tools to automate the O2C process - invoicing, cash application, dunning, reconciliation.
• Enhance credit decisioning - replace today's manual spreadsheet workflow with a system-driven process for credit checks, payment-method routing, and credit-limit monitoring.
• Partner with Product, Engineering, and Operations to build the invoicing path for VMS customers, including rate/hour/worker/shift reconciliation and hold-enforcement tooling.

About The Role

Our customer mix has scaled faster than our finance and revenue operations, and we are hiring an Order-to-Cash Lead to take ownership of the full O2C function - strategy, execution, AI-powered automation and tooling.

Required Qualifications

• 7+ years in AR, billing, collections, credit, or O2C — with hands-on AND strategic experience. You can run a customer escalation and design a policy in the same week.
• Track record of standing up or significantly improving credit and hold policies, including the cross-functional negotiation with Sales/AM that comes with it.
• Comfortable managing an outsourced AR/collections team or BPO — setting KPIs, holding them accountable, and escalating issues effectively.
• Familiarity with VMS/MSP customer chains or comparable third-party-payer environments, and with PO-driven billing workflows.
• Direct experience partnering with Product/Engineering to scope and ship finance tooling — not just opening tickets.
• Strong analytical fluency: QBO / NetSuite, AR dashboards, DSO and bad-debt KPIs, borrowing-base reporting.
• Operates well in a high-growth, high-ambiguity environment. Marketplace, staffing, or labor-platform

Competitive base salary

• + equity in a high-growth, venture-backed company
• Hybrid work culture with office in

SF

• In-person company off-sites
• Medical, dental & vision coverage
• Unlimited PTO
• 401(k)

WFH stipend to support your home office setup

WorkWhile has a diverse, mission-driven, and supportive culture—we look for people who want to take ownership, are energized by ambiguity, and strive to make a lasting impact. If this resonates with you, we’d love to chat!