Finance Automation Lead

Instawork is on a mission to create meaningful economic opportunities for skilled hourly professionals in communities around the globe. Our AI-powered labor marketplace helps local businesses scale, and enables global technology companies to push the frontiers of robotics and AI. Backed by world-class investors like Benchmark, Spark Capital, Craft Ventures, Greylock, Y Combinator, and others, we’re looking for exceptional talent to reimagine the way the world works.

We're looking for a builder to own Instawork's order-to-cash process and lead finance automation across the Finance team. The role is split roughly evenly: half on billing, collections, and cash conversion, and half on automating finance workflows beyond accounts receivable (AR), from close and reconciliations to Accounts Payable, treasury, and reporting. You'll oversee our offshore collections analysts, work directly with Account Managers, Sales and our business partners (customers) on billing and collection issues, and build AI-powered workflows that cut manual work across Finance.

You'll start hands-on to learn how each process runs, then redesign it so it runs with far less manual effort. This position reports directly to the Controller and is based in our San Francisco office (downtown near public transit) and follows an onsite work model, requiring in-office presence 5 days a week.

• Own the collections strategy and the AR balance, with DSO and the cash conversion cycle as the main measures, and run a weekly cash review with Finance leadership.
• Work directly with Sales, Account Management, and our business partners to resolve billing questions, disputes, and past-due balances. Serve as the escalation point for enterprise, MSA, and VMS accounts.
• Find the root causes of late cash, such as billing errors, account setup that doesn't match the contract, portal approval delays, and drive fixes with Sales, Ops, and Product.
• Own invoicing setup QA and cash application, and support month-end close with AR reconciliations and reserves.
• Oversee and coach our collections analysts in the Philippines, setting priorities and performance expectations and shifting their work toward exception handling as automation takes over the routine flow.
• Establish, maintain and own the credit approval process including running credit checks and working with Sales on creative credit options for potential new partners (customers)
• Build AI agents and workflows for collections prioritization and outreach, remittance matching, dispute triage, VMS portal tracking, and pre-send invoice checks.

• Partner with the Accounting & FP&A (Finance) team to map manual workflows, rank automation opportunities by time saved and risk reduced, and manage a prioritized backlog.
• Build and deploy AI/LLM-powered agents and workflows across Finance, such as bank and balance sheet reconciliations, journal entry preparation, accruals, close task tracking, and variance analysis.
• Automate procure-to-pay and spend workflows, including invoice intake and coding, approvals, vendor onboarding, and payment runs.
• Automate cash reporting, including daily cash positions, bank and payout reconciliations, cash forecast inputs, and lender compliance reporting.
• Build integrations and data flows between Net Suite, our billing and payment systems, banks, and BI tools, and replace manual spreadsheets with automated dashboards and reports.
• Design human-in-the-loop controls, audit trails, and documentation so automated outputs are accurate, auditable, and ready for external audit.
• Train the Finance team on new tools, write runbooks, and own what you ship in production.

• Recent, demonstrable experience building AI/LLM-powered or agentic workflows that run in a real operation and that people still use.
• Working knowledge of core finance processes (order-to-cash, procure-to-pay, month-end close, reconciliations) and how they connect to the ERP.
• Strong quantitative and problem-solving skills with advanced Excel/Google Sheets.
• Experience with workflow automation or integration tools (e.g., Workato, Zapier, n8n, Make) or APIs.
• Experience leading or developing people, including remote or offshore teams.
• Confidence working directly with customers and Sales on billing and collection issues, and influencing teams you don't manage.
• Ownership, urgency, and comfort working on messy, ambiguous problems in a fast-paced environment.
• Nice to have experience in AR, billing,…