AI Chief of Staff
About
Product.ai is the truth layer for commerce. The AI Chief of Staff is the operational right hand to the founder, owning the company's operational outcomes end to end while running AI agents to move them. The company is profitable, bootstrapped, with 20 employees, no outside investors or board.
The Role
Own end-to-end operational outcomes and run long-lived AI agents to move them. Improve recruiting funnel throughput, operate an ownership-equity program, manage company cadence, vendors, and workplace, and instrument agent compute and outcomes. Success is measured on outcome movement and CEO decision capacity returned.
The System You'll Need to Model
- A recruiting funnel processing ~1,400 candidates with AI evaluating the top and humans as the bottleneck
- CEO attention as the scarcest resource, managing decision routing among CEO, you, and AI agents
- An ownership program with real equity mechanics including Profits Interest Units, tender offers, and profit sharing
- Company operating with AI agents at scale, tracking compute costs vs. business outcomes
- A company operating system with falsifiable outcomes, consent-based records, and automated architectural decision enforcement
- Regular revision of the operating model requiring foresight and independent modeling
What You Will Own
- Operational outcome loops with falsifiable tests and independent verification
- Recruiting pipeline throughput focusing on candidate-to-decision latency
- Ownership-program operations managing equity grant cycles, vesting, tender logistics, and communication
- Company cadence, office, and vendors management with explicit decision authority and spending controls
Who You Are
You form working models of complex systems, quickly update them, turn ambiguity into measurable systems, own CEO leverage as a product, work fluently between strategy and operations, write clearly, build with and manage AI agents, and think in tests and guardrails.
You have built operational systems moving from scrappy to structured, such as automations retiring manual processes, instrumented hiring pipelines, or vendor/finance workflows with real money moving through them.
Employment Details
- Location: Los Angeles, CA, USA
- Workplace Type: Hybrid
- Salary: 200K-400K Annually
- Employment Level: Expert/Leader
Product.ai is building the verification layer for AI commerce. We verify what AI cannot: whether a coupon actually works, whether a price is actually current, whether a product claim is actually true. Our systems process billions of real-time commerce signals to produce verified, ground-truth data at scale. Our products - SimplyCodes (400K+ stores, used by millions) and Product.ai (AI shopping agent) - drive over $1B in annual e-commerce by giving consumers and AI agents something no language mo
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