Finance Automation Lead

Instawork; San Francisco (CA); On-site; USD 110,000 - 140,000; Full time

Benefits offered by this job

Medical insurance

Dental insurance

Vision insurance

Flexible paid time off

8 paid company holidays annually

Phone stipend

Commuter stipend

HSA contributions

401K plan

Stock options

Perkspot discount program

Job summary

Instawork is seeking a hands-on leader to own the order-to-cash process and drive finance automation across the Finance team. The role splits roughly 50/50 between billing/collections and automating finance workflows beyond AR, including close, reconciliations, AP, treasury, and reporting.

You will work with Sales, Account Managers, and business partners to optimize processes and implement AI-powered workflows.

Qualifications

• 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.
• Familiarity with internal controls, SOX, or supporting external audits.

Responsibilities

• Own the order-to-cash and collections strategy; manage AR balance, DSO, and cash conversion cycle.
• Collaborate with Sales, Account Management, and business partners to resolve billing questions, disputes, and past-due balances.
• Identify root causes of late cash and drive fixes with Sales, Ops, and Product.
• Oversee invoicing setup QA, cash application, and month-end close support with AR reconciliations.
• Coach offshore collections analysts and shift routine work toward automation.
• Own credit approval process and work with Sales on credit options for new partners.
• Build AI agents and workflows for collections prioritization, remittance matching, and disputes.

Skills

AI/LLM-powered workflows

Finance automation

Order-to-Cash (O2C)

Cash collection & AR

Automation backlog management

People leadership

Tools

NetSuite

Upflow

Salesforce

VMS portals (Fieldglass, Beeline, Coupa, Ariba)

BI tools

Job description

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.

What You'll Do:

Order-to-Cash & Collections (~50%)

• 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.

Finance Automation (~50%)

• 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 NetSuite, 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.

Who You Are:

• 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, collections, or broader finance operations
• Familiarity with systems such as NetSuite, Upflow, Salesforce, or VMS and procurement portals (e.g., Fieldglass, Beeline, Coupa, Ariba).
• Familiarity with internal controls, SOX, or supporting external audits.

For CA Based Applicants:

• The base salary for this position is between $110K to $140K
• This position is eligible for equity in the form of stock options
• This position is eligible for Instawork benefits, including:
• Variety of medical, dental, and vision plans with coverage beginning on the date of hire
• Flexible paid time off
• At least 8 paid company holidays annually
• Phone stipend
• Commuter stipend
• Supplemental pay on qualified leaves
• Employee health savings accounts (HSA) contribution
• Flexible spending plans
• 401K plan
• Perkspot - discount program through Lumity

#LI-Onsite

Our Values

Empathy, Trust & Candor
We put ourselves in the shoes of our colleagues and customers and don’t shy away from uncomfortable conversations, instead building trust through honest and direct feedback.

Bias for Action
We practice high-velocity decision-making, clear-eyed that we often operate with incomplete information. Growing quickly means it’s OK to be wrong, so long as we learn from our mistakes and course correct!

Always Be Learning
We’re a curious bunch, and with AI transforming our workplace we encourage everyone to learn from each other, compounding our knowledge and experience to help us change an entire industry.

Act Like an Owner
We work long, hard, and smart, building products that delight our users and drive growth. Your ability to impact Instawork is limited only by your courage and conviction, not your job description.

About Instawork

Founded in 2015, Instawork is the nation’s leading online labor marketplace for food services, hospitality, light industry, and logistics, connecting more than 7M skilled workers with local restaurants, hotels, warehouses, stadiums, and more. Our AI-powered platform serves thousands of businesses across more than 50 major markets in the United States and Canada. We're not just helping fill shifts, we're supporting local economies—and we're just getting started!

Instawork has been featured by CBS News, The Wall Street Journal, The Washington Post, and the Associated Press. Forbes included us on their Next Billion Dollar Startups list; RetailTech Breakthrough named us Workforce Hiring Solution of the Year for 2025; and Inc. 5000 recognized us as one of the country's top 10% fastest-growing companies two years in a row. But what matters most is our impact. We're solving real problems for real people, and we’re doing it at scale.

Join our team to help us build something that matters! We’re looking for superstars who want to help us shape the future of work. With hubs in San Francisco, Bangalore, and Chicago, city offices in New York, Phoenix, and Singapore, we're back to working together in-person five days a week because we believe the best ideas happen when great people collaborate face-to-face. We also value diverse perspectives and encourage applications from candidates of all backgrounds.