Order to Cash Lead

About WorkWhile

WorkWhile is an AI-native labor platform serving enterprise customers across logistics, food production, retail, hospitality, events, and managed services. WorkWhile identifies the best hourly workers and matches them with shifts that fit their skills, location, and life. Businesses get access to a quality workforce, while workers get stable income and unmatched benefits, including next day pay, free telehealth services, and financial services.

We have the audacious goal to align incentives and solve inefficiencies in the labor market, disrupting the $650 billion staffing and recruiting market. Backed by Khosla Ventures and recognized by the Inc. 5000 for 10x growth, WorkWhile is reshaping the future of work.

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.

What You'll Own

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.

Who You Are

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

Compensation & Benefits

• 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!