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WorkWhile is a venture-backed workforce platform (backed by Khosla Ventures, Inc. 5000 10x growth) that matches enterprise customers across logistics, food production, retail, hospitality, events, and managed services with hourly workers. The company is evolving from a high-growth temporary labor marketplace into a comprehensive platform with fintech offerings, creating a complex financial landscape.
You will own the full Order-to-Cash (O2C) function, spanning strategy, execution, AI-powered automation, and tooling. This is a hands-on leadership role managing both strategic initiatives and day-to-day operations.
STRATEGY & POLICY: Establish WorkWhile's standard invoicing and payment terms. Review non-standard contract terms and partner with Sales on exception paths. Operationalize credit policy, including decisions on invoicing vs. pay-by-bank/credit card, credit-limit setting, and hold policies. Partner with the CFO on cash-flow implications, AR aging, line of credit, borrowing base, and DSO trajectory.
OPERATIONS & EXECUTION: Manage WorkWhile's outsourced AR and collections team, setting operating cadence, metrics, and customer prioritization. Drive the open backlog and partner with account executives and account managers on aged AR. Enforce holds when warranted and run the weekly AR/AM/Finance forum. Vet and onboard third-party collection agencies, defining escalation criteria and contract terms.
PRODUCT & ROADMAP: Leverage AI-native tools to automate the O2C process. Automate credit decisioning to replace manual spreadsheets with system-driven workflows. Partner with Product & Engineering to automate invoicing (billing generation, customer-portal delivery, PO matching, cash application). Collaborate on invoicing paths for VMS customers, including PO match, worker-ID reconciliation, and rate-delta detection. Sequence the roadmap with CFO and Engineering leadership, owning requirements, acceptance, and rollout.
REQUIREMENTS:
- 7+ years in AR, billing, collections, credit, or O2C with both hands-on and strategic experience
- Familiarity with AI-native finance automation tools and products
- Track record of standing up or significantly improving credit and hold policies, including cross-functional negotiation with Sales/AM
- Experience managing outsourced AR/collections teams or BPOs, setting KPIs and holding them accountable
- Familiarity with VMS/MSP customer chains or comparable third-party-payer environments and PO-driven billing workflows
- Direct experience partnering with Product/Engineering to scope and ship finance tooling
- Strong analytical fluency: QuickBooks Online / NetSuite, AR dashboards, DSO and bad-debt KPIs, borrowing-base reporting
- Ability to operate in high-growth, high-ambiguity environments. Marketplace, staffing, or labor-platform experience is a plus.
