--- title: "Order to Cash Lead" company: "WorkWhile" company_url: "https://www.remjobs.works/companies/workwhile" url: "https://www.remjobs.works/job/workwhile-order-to-cash-lead-824b6276-d8ee-4bf4-aa41-3dcffdd60630" apply_url: "https://jobs.ashbyhq.com/workwhilejobs/d507b2f2-d3d4-4f41-9b55-887745ef09e3" workplace: hybrid location: "San Francisco" employment_type: full-time seniority: lead role: other region: united-states date_posted: 2026-09-22T15:56:14.372Z first_seen_by_remjobs: 2026-09-22T16:11:45.149Z --- # Order to Cash Lead **WorkWhile** · San Francisco Apply: https://jobs.ashbyhq.com/workwhilejobs/d507b2f2-d3d4-4f41-9b55-887745ef09e3 ## About WorkWhile Hire event staff and warehouse talent near you, fast. WorkWhile connects businesses with reliable, flexible professionals for logistics, production, and events. ## About the role #### 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!* --- Source: WorkWhile's own career page, read by RemJobs. Canonical HTML version: https://www.remjobs.works/job/workwhile-order-to-cash-lead-824b6276-d8ee-4bf4-aa41-3dcffdd60630