Order to Cash Lead
About the job
- 7+ years in accounts receivable, billing, collections, credit, or Order to Cash, with hands-on and strategic experience.
- A track record of standing up or significantly improving credit and hold policies, including cross-functional negotiation with Sales and Account Management.
- Experience managing an outsourced accounts receivable or collections team or business process outsourcing provider, including setting key performance indicators, holding the provider accountable, and escalating issues effectively.
- Familiarity with vendor management system or managed service provider customer chains, or comparable third-party-payer environments, and purchase-order-driven billing workflows.
- Direct experience partnering with Product or Engineering to scope and ship finance tooling.
- Strong analytical fluency with QuickBooks Online or NetSuite, accounts receivable dashboards, days sales outstanding and bad-debt key performance indicators, and borrowing-base reporting.
- Ability to operate effectively in a high-growth, high-ambiguity environment, preferably in a marketplace, staffing, or labor-platform context.
- Own the end-to-end Order to Cash process, including strategy, execution, AI-powered automation, and tooling.
- Maintain the standard invoicing and payment-terms framework, review non-standard contract requests, and partner with Sales on the defined exception path.
- Optimize credit policy, including customer payment-method decisions, credit-limit setting, and hold policy.
- Partner with the Chief Financial Officer on cash-flow and financing implications of accounts receivable aging, the company line of credit, borrowing base, and days sales outstanding trajectory.
- Manage the outsourced accounts receivable and collections team by setting operating cadence, metrics, and customer prioritization.
- Drive the open accounts receivable backlog, partner with Account Executives and Account Managers on aged receivables, and resolve customer-specific issues.
- Enforce customer holds when warranted and run the weekly accounts receivable, Account Management, and Finance process where holds are decided.
- Own vendor management system customer invoice reconciliation end-to-end, partner with Operations on root-cause resolution, manage credit and payment-allocation reconciliation, ensure WorkWhile invoices, customer vendor management system invoices, and QuickBooks Online financials reconcile, and drive Engineering to build automation and application programming interface connections between systems.
- Represent Finance externally on new customer invoice requirements and requests and own customer escalations on disputes and issues.
- Serve as Finance Administrator for the internal Admin Portal and configure policies affecting customer invoicing.
- Use AI-native tools to automate invoicing, cash application, dunning, and reconciliation.
- Enhance credit decisioning by replacing the manual spreadsheet workflow with a system-driven process for credit checks, payment-method routing, and credit-limit monitoring.
- Partner with Product, Engineering, and Operations to build the invoicing path for vendor management system customers, including rate, hour, worker, and shift reconciliation and hold-enforcement tooling.
About the company
WorkWhile connects businesses that need hourly workers with vetted labor in sectors like warehouse, light industrial, last-mile delivery, event services, food production, and hospitality. The platform uses advanced screening and background checks to verify workers and lets businesses set an hourly rate for each worker, paying only for filled jobs. The system enables flexible staffing, letting companies scale labor up or down as needed. Workers can manage pay, schedules, and preferences via a mobile app, including next-day pay to shorten the typical payday delay. Revenue comes from charging businesses for the labor provided, with no upfront costs, hidden fees, or long-term contracts. The goal is to efficiently match demand for hourly labor with a reliable, vetted workforce while giving both sides flexibility and cost control.
Company Size
201-500
Company Stage
Series B
Total Funding
$39.5M
Headquarters
San Francisco, California
Founded
2019
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Simplify's Take
What believers are saying
- September 2026 warehousing deployments cut short-notice absences by over 50% and call-outs below 3%.
- WorkWhile reported 1.2 million workers and 110% revenue growth in early 2026.
- CEO Simon Khalaf, appointed February 2026, pushes enterprise expansion, real-time pay, and financial services.
What critics are saying
- San Francisco's January 2026 settlement cost $4.5 million and left post-September 2025 claims open.
- California misclassification enforcement can force reclassification, back pay, and compliance costs across WorkWhile's core model.
- If courts and regulators ban contractor-like staffing economics, WorkWhile loses pricing leverage and market access.
What makes Workwhile unique
- WorkWhile sells AI-native staffing with Employer of Record compliance, not simple shift posting.
- September 8, 2026 expansion adds full-scale staffing and net-30 financing across verticals.
- WorkWhile Coach and Certified Professional Program turn worker assessment into deployable labor credentials.
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Benefits
Health, vision, & dental premiums
Unlimited time off
Referral bonus
WFH expenses
Growth & Insights and Company News
6 month growth
↑ 0%1 year growth
↑ 0%2 year growth
↑ 1%WorkWhile has expanded its AI-native platform from on-demand shift coverage to a full-scale staffing solution. The company aims to reduce the $225.8 billion annual cost of worker absenteeism in the US by half. Early deployments in warehousing have cut short-notice absences by more than 50%. The platform automatically backfills open full-time shifts with on-demand staff using AI models. Initial implementations achieved 24-hour notice call-out rates below 3%, compared to the Harvard-measured median of 6.2% to 6.5%. The expanded service offers net 30 payment terms for companies whilst maintaining real-time pay for workers. WorkWhile serves industries including warehousing, light industrial, logistics, hospitality, and food production, acting as employer of record.
WorkWhile, an AI-native labour platform, has licensed technology assets from Mindy, an email-first AI agent platform, with Mindy's technical team joining WorkWhile's product and engineering divisions. The transaction aims to scale AI-native agents across labour-intensive sectors and optimise operational automation for human resources, operations and middle management. Mindy, founded in 2023 and backed by Sequoia Capital and Founders Fund, developed asynchronous AI agents for executive administration and enterprise workflows. Its founding team includes veterans from PayPal and YouTube. WorkWhile is also creating a Frontline Deployment Engineering Team to integrate AI-native workforce automation into enterprise infrastructures. The company, funded by Khosla Ventures and others, serves 1.3 million workers and aims to bring financial stability to 80 million US hourly workers.
WorkWhile, an AI-powered labour platform, has launched WorkWhile Money, an earning management solution for the US hourly workforce. The platform integrates with WorkWhile's existing application, providing workers with tools to manage, project and secure their earnings. WorkWhile Money uses proprietary labour prediction models to forecast workers' future cash flow based on shift availability, skills and historical patterns. The platform features a real-time earnings dashboard and prospective cash flow forecasts, enabling workers to plan based on expected income rather than generalised models used by traditional banks. Built in partnership with Highnote, the service allows workers instant access to earnings after each approved shift. WorkWhile Money works with workers' existing bank accounts, requiring no new accounts or institutional changes. The company plans to expand into savings guidance and additional financial health tools.
WorkWhile, an AI-native labour platform for hourly workforce management, has appointed James Everingham to its board of directors. Everingham is CEO of Guild AI and previously served as vice president of engineering at Meta Devinfra, where he led large-scale infrastructure and AI systems. The appointment comes as WorkWhile expands its AI capabilities, including operational digital twins that simulate workforce conditions, real-world AI models for scheduling and retention, and enterprise governance tools. The platform serves retail, logistics, light industrial and hospitality sectors. WorkWhile combines operational data, automation and simulation tools to improve staffing reliability and workforce planning. The company is backed by Khosla Ventures, Citibank Impact Fund, Reach and Rethink Impact.
WorkWhile, an AI-powered labour platform connecting businesses with hourly workers, has launched WorkWhile Coach, an AI talent agent that assesses worker skills and matches them with job opportunities across multiple companies. The system conducts conversations with workers to identify their experience and capabilities, including skills they may not have considered. Unlike traditional hiring software that filters applicants, Coach aims to uncover workers' abilities and connect them to roles where those skills are valued. The first application will be WorkWhile's Certified Professional Programme for hospitality workers, which evaluates knowledge through interactive assessments rather than relying solely on CVs. Final hiring decisions remain with human managers. WorkWhile reported 110% revenue growth over the past nine months and currently provides staffing for stadiums, convention centres and universities across the United States.