Head of Finance
Smallest • San Francisco, CA • Full Time
Posted on Thu, May 28, 2026
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.