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!