Order to Cash Lead

WorkWhile•San Francisco, CA

1d•Hybrid

About The Position

WorkWhile is seeking an Order-to-Cash Lead to take ownership of the full O2C function, including strategy, execution, and AI-powered automation. This role will be responsible for managing the end-to-end Order to Cash process with a growth mindset, identifying and fixing issues, and thinking strategically about long-term process health and scalability. The lead will also manage the outsourced AR and collections team, drive the open backlog, own VMS customer invoice reconciliation, and represent Finance externally on new customer invoice requirements. Additionally, the role involves leveraging AI-native tools to automate the O2C process and enhancing credit decisioning. This is a key role in a high-growth, venture-backed company reshaping the future of work.

Requirements

7+ years in AR, billing, collections, credit, or O2C — with hands-on AND strategic experience.
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 experience.

Responsibilities

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.
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.
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.