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Salary: USD 110,000 - 140,000 / annual
Instawork, a leading AI-powered labor marketplace connecting skilled workers with local businesses across 50+ markets in the US and Canada, is seeking a Finance Automation Lead to own the order-to-cash process and drive finance automation across the Finance team.
The role is split roughly evenly between two core areas:
**Order-to-Cash & Collections (~50%)**
You will own Instawork's collections strategy and AR balance, with DSO and cash conversion cycle as primary metrics. You'll run weekly cash reviews with Finance leadership, work directly with Sales, Account Management, and business partners to resolve billing questions and past-due balances, and serve as the escalation point for enterprise, MSA, and VMS accounts. You'll identify root causes of late cash (billing errors, account setup mismatches, portal delays) and drive fixes across Sales, Ops, and Product. Responsibilities include invoicing setup QA, cash application, month-end AR reconciliations, and reserves. You'll oversee and coach collections analysts in the Philippines, shifting their work toward exception handling as automation takes over routine flows. You'll establish and own the credit approval process, including credit checks and working with Sales on creative credit options. You'll build AI agents and workflows for collections prioritization, remittance matching, dispute triage, VMS portal tracking, and pre-send invoice checks.
**Finance Automation (~50%)**
You'll partner with the Accounting & FP&A team to map manual workflows, rank automation opportunities by time saved and risk reduced, and manage a prioritized backlog. You'll build and deploy AI/LLM-powered agents and workflows across Finance, including bank and balance sheet reconciliations, journal entry preparation, accruals, close task tracking, and variance analysis. You'll automate procure-to-pay and spend workflows (invoice intake, coding, approvals, vendor onboarding, payment runs), cash reporting (daily positions, reconciliations, forecasts, lender compliance), and build integrations between NetSuite, billing systems, banks, and BI tools. You'll replace manual spreadsheets with automated dashboards and reports, design human-in-the-loop controls and audit trails for accuracy and auditability, train the Finance team on new tools, and own what you ship in production.
This position reports directly to the Controller and is based in the San Francisco office (downtown near public transit) with a full 5-day onsite work model.
**Requirements:**
- Recent, demonstrable experience building AI/LLM-powered or agentic workflows that run in real operations and are actively used
- 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 proficiency
- 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: AR, billing, collections, or broader finance operations experience
- Nice to have: Familiarity with NetSuite, Upflow, Salesforce, VMS and procurement portals (Fieldglass, Beeline, Coupa, Ariba)
- Nice to have: Familiarity with internal controls, SOX, or supporting external audits
