Chief of Staff to the CEO - Builder-Orchestrator

• An AI operating system called Cortex that the entire team works inside - outcomes shipping sessions people profiles strategic intelligence. You'll operate this system and extend it.
• A recruiting pipeline processing 800+ candidates across 10+ roles. Gauntlet screening chemistry calls paid trial contracts. You'll coordinate the moving parts.
• Vendor and contract management across legal insurance office and service providers. You own the operational surface the CEO shouldn't be touching.
• A company where 20% of work is delegatable to AI agents and 80% still requires human judgment. You need to know which is which - and build the automation for the 20%.

• Operational cadence. The rhythms that keep a 25-person team coordinated without bureaucracy: weekly cycles quarterly planning cross-team visibility. You build the system not the process.
• Internal tooling and automation. When something is done manually three times you build the automation. First-principles approach - you code or configure not just specify.
• Recruiting operations. Coordinate the pipeline - scheduling candidate communication trial logistics onboarding. Not recruiting strategy (that's the CEO) but the operational machinery that makes it work.
• Vendor and administrative operations. Contracts insurance office logistics service providers. The operational substrate that lets everyone else focus on product.

• How you think. You see systems before you see tasks. When you encounter a manual process your first thought is "how do I automate this?" not "how do I do this faster." You think about leverage - which 20% of effort produces 80% of value.
• How you work. You build before you hire. You write scripts configure tools and ship internal dashboards before asking for headcount. You can read and write code - maybe not production backend but internal tools automations data pipelines. AI tools (Claude Code Cursor) are part of your daily workflow.
• What you've probably built. Internal systems at a company that scaled from scrappy to structured. You've personally automated workflows that saved meaningful time. You've managed vendors contracts and operational complexity. We care about what you built and what it replaced not where you did it.
• Who this isn't for. This role is wrong if your primary skill is "setting up Asana" or "managing a calendar." It's wrong if you expect to delegate to a team immediately. It's wrong if you need clear role boundaries - this role is the boundary between what the CEO does and what the system handles. You'll thrive here if you like building operational infrastructure that makes a small team feel like a large one.

• Total first-year comp: $300000 - $400000 (base + equity + profit sharing).
• Base: $200000 - $250000. Top of market for operations at this level.
• Equity: Profits Interest Units (PIUs) - Class B Membership Interests at $0 strike price. Actual ownership from day one. Capital Gains tax treatment.
• Profit sharing: Annual pro-rata share of free cash flow. Real cash every year.
• Liquidity: Annual tender offer. Real cash every year. No IPO required.
• Benefits: 100% premium coverage. Unlimited PTO.

What We Do

Product.ai (formerly Demand.io) is the truth layer for commerce. Built on Axiomatic Intelligence — a proprietary adversarial reasoning methodology that stress-tests product claims against physics economics and engineering constraints — Product.ai delivers verified purchase verdicts not summaries. Product.ai tells consumers when NOT to buy. Product.ai emerges from Demand.io a profitable bootstrapped AI commerce company whose SimplyCodes platform processes over $1B in annual transaction value with a team of 20. Founded by Michael Quoc.

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