Order to Cash Lead

WorkWhile•San Francisco, CA

1d•Hybrid

About The Position

WorkWhile is seeking an Order-to-Cash Lead to take full ownership of the O2C function, including strategy, execution, and the implementation of AI-powered automation and tooling. The company is experiencing rapid growth and needs to scale its finance and revenue operations to match. This role will be instrumental in reshaping the company's financial landscape as it evolves into a comprehensive workforce platform with fintech offerings for workers. WorkWhile is backed by Khosla Ventures and has been recognized for its significant growth.

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 establishing or significantly improving credit and hold policies, including cross-functional negotiation with Sales/AM.
Comfortable managing an outsourced AR/collections team or BPO, setting KPIs, holding them accountable, and escalating issues.
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.
Strong analytical fluency with QBO/NetSuite, AR dashboards, DSO and bad-debt KPIs, and borrowing-base reporting.
Ability to operate well in a high-growth, high-ambiguity environment.

Nice To Haves

Marketplace, staffing, or labor-platform experience is a plus.

Responsibilities

Establish WorkWhile’s standard invoicing and payment terms.
Review non-standard invoicing and payment terms in incoming contracts and partner with Sales on an exception path.
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 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, setting operating cadence, metrics, and customer prioritization.
Drive the open backlog and partner with AEs and AMs on aged AR, resolving customer-specific issues.
Enforce holds when warranted and run the weekly AR/AM/Finance forum for hold decisions.
Vet and onboard a third-party collection agency, defining escalation criteria, contract terms, and ongoing relationship.
Leverage AI-native tools to automate the OTC process.
Automate credit decisioning, replacing manual processes with a system-driven workflow for credit checks, payment-method routing, and credit-limit monitoring.
Partner with Product & Engineering to automate invoicing, including 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, owning requirements, acceptance, and rollout.