Chief of Staff to the CEO — Builder-Orchestrator

Product.ai is building the truth engine for shopping. Profitable. Bootstrapped. No outside investors. No board. 25 people outperforming companies 10x our size.

We're hiring a Chief of Staff to the CEO.

Why This Role Exists

The CEO runs product strategy, engineering direction, recruiting, and company operations simultaneously. That works at 15 people. At 25 - with three product surfaces live, a trial-contract hiring pipeline, and an AI operating system powering everything - the operational surface area exceeds what one person can hold. Someone needs to run cadence, ship internal tooling, manage vendor relationships, and orchestrate the systems that keep a high-velocity small team coordinated.

This is not an administrator role. This is a builder-orchestrator. You design automation, not process. You ship tooling, not slide decks.

The System You'll Need to Model

• 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%.

What You Will Own

• 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.

Who You Are

• 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.

How We Evaluate

Written artifact. A system, process, or automation you built. Show us the before and after.

Video screen. How you think about operational problems and when NOT to use AI for a task.

Conversation with the founder. How you model a company's operational needs and decide what to build vs. delegate vs. ignore.

30-day paid trial. Audit existing workflows. Identify the top 3 to automate. Ship one automation by day 30. This is the test.

Compensation & Ownership

• Total first-year comp: $300,000 - $400,000 (base + equity + profit sharing).
• Base: $200,000 - $250,000. 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.

Based in Santa Monica. Primarily in-office - this role requires daily coordination proximity.

Apply here: https://product.ai/join/chief-of-staff

Include a written artifact showing something you built that made an organization run better.