Head of Finance

Head of Finance Location: San Francisco, CA (Hybrid) Postion: Permanent About us: smallest.ai is building next-generation AI voice agents that power intelligent customer conversations for enterprises in BFSI, financial services, and fintech. Our team works across speech, LLMs, and real-time AI systems to help businesses automate complex interactions at scale. We are backed by strong Silicon Valley investors and are scaling rapidly across the US and India. We are looking for a Head of Finance who can own the full scope of finance, accounting, and operations end-to-end, from FP&A and cash management to payroll, HR administration, and legal and compliance matters. You've thrived in fast-paced startup environments before, and you're ready to do it again, contributing meaningfully from the start. This role is ideal for someone who thinks in first principles, takes pride in financial accuracy, and wants to be deeply embedded in a fast-growing startup. What You'll Do Build and maintain driver-based financial models across revenue, costs, margin, and cash flow Own cash flow forecasting, month-end close, revenue recognition, and balance sheet reconciliations Prepare monthly, quarterly, and annual management reporting; distill insights and flag risks Partner with the CEO on strategic decisions around hiring, investment, and capital deployment Manage relationships with outsourced accounting, tax, and payroll vendors Own accounts payable, corporate cards, expense management, and financial controls Support HR operations including payroll and benefits Coordinate with outside legal counsel on contracts, vendor agreements, and compliance Own office operations and facilities for our hybrid SF team What We're Looking For 6+ years of progressive finance experience at a high-growth, venture-backed or bootstrapped startup Demonstrated ability to own FP&A end-to-end: modeling, forecasting, close, and reporting Meaningful use of AI tools to rethink and redesign finance workflows Experience with enterprise AI/SAAS businesses Strong command of US GAAP, revenue recognition, and financial reporting best practices Proficiency with QuickBooks Online and strong Excel/Google Sheets modeling skills Comfortable moving between strategic analysis and detailed operational work CPA or experience managing outsourced accounting and tax vendors is a plus Why Join smallest.ai Be the senior-most finance hire at a rapidly scaling enterprise AI company Work directly with the CEO on decisions that shape how the business grows Join a high-ownership culture where your work has immediate, visible impact If you're excited to own finance at a company building at the frontier of AI, we'd love to hear from you.

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