Order to Cash Lead

About WorkWhile

WorkWhile is on a mission to help workers earn a better living and live better lives. More than 80 million Americans work hourly jobs - often with unpredictable schedules, near-minimum wages, and few benefits - leading to real financial instability. We're fixing that by matching enterprise customers across logistics, food production, retail, hospitality, events, and managed services with a quality hourly workforce, while giving workers stable income and unmatched benefits like next-day pay, free telehealth, and financial services.

WorkWhile is evolving from a high-growth temporary labor marketplace into a comprehensive workforce platform for enterprises with fintech offerings workers. The result is a multi-business-model company with a genuinely complex, interesting financial landscape.

Backed by Khosla Ventures and recognized by the Inc. 5000 for 10x growth, WorkWhile is reshaping the future of work.

The Opportunity

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

• Establish WorkWhile's standard invoicing and payment terms
• Review non-standard invoicing and payment terms in incoming contracts; partner with Sales on a defined exception path
• Operationalize 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, the metrics, and the customer prioritization
• Drive the open backlog; partner with AEs and AMs on aged AR; bring customer-specific issues to resolution
• Enforce holds when warranted. Run the weekly AR/AM/Finance forum where holds are decided
• Vet and onboard a third-party collection agency for accounts that have exhausted internal collections; define the escalation criteria, the contract terms, and the ongoing relationship

Product & roadmap

• Leverage modern AI-native tools to automate the OTC process
• Automate credit decisioning - replace today's manual spreadsheet with a system-driven workflow for credit checks, payment-method routing, and credit-limit monitoring.
• Partner with Product & Engineering to automate invoicing - billing generation, customer-portal delivery, PO matching, and cash application.
• Collaborate with Product, Engineering, and Operations to build the invoicing path for VMS customers - including PO match, worker-ID reconciliation, and rate-delta detection.
• Sequence the roadmap with the CFO and Engineering leadership; own the requirements, the acceptance, and the rollout.

What We're Looking For
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.
• Acquired familiarity with AI-native finance automation tools and products
• 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 is a plus.

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!