AI Systems Associate — Office of the CEO

Los Angeles

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 an **AI Systems Associate**. **Why This Role Exists** Product.ai runs on an AI operating system (AIOS) that coordinates outcomes, people, shipping, and strategic intelligence across a 25-person team. The CEO is currently the primary operator of this system alongside his product and strategy work. As the system scales, it needs a dedicated operator-builder who can run it, extend it, and make it more powerful --- someone who lives inside the system daily and sees what it needs before being told. **The System You'll Need to Model** * **AIOS** --- a shared operating system where the team tracks outcomes, ships work, manages people profiles, and grounds every Claude Code session in strategic context. You'll operate and extend it. * **A recruiting pipeline** with 800+ candidates, automated screening (AIRS), trial contracts, and project-based evaluation. You'll coordinate and improve the machinery. * **A CEO who operates at 2am-8am and ships across multiple domains simultaneously.** You'll need to model his direction independently and prepare the operational ground before he asks. * **An AI-augmented workflow** where Claude Code and Cursor are primary tools, not supplements. You'll work inside Claude Code daily. **What You Will Own** * **AIOS operations.** Daily operation of the team's AI operating system --- data quality, pipeline health, dashboard accuracy, cron job monitoring. You're the person who notices when something breaks before it becomes visible. * **CEO operational leverage.** The CEO's force multiplier for operational tasks --- recruiting coordination, meeting prep, vendor management, research briefs, internal communications. You anticipate what's needed and prepare it. * **System extension.** When a new process is needed, you build it inside AIOS --- a new dashboard module, a new cron job, a new data pipeline. You code in Python and work fluently in Claude Code. **Who You Are** * **How you think.** You're a systems thinker. You see how the parts connect. When something is inefficient, you don't just notice it --- you model why it's inefficient and build the fix. You learn new systems fast --- you could pick up AIOS in days, not months. * **How you work.** You're proactive to the point of being predictive. You prepare materials before they're requested. You see the CEO's trajectory and get ahead of it. AI tools are your primary workflow --- you use Claude Code and Cursor daily, not as novelties but as production systems. * **What you've probably done.** Operated at the intersection of strategy and execution --- maybe as a chief of staff, operations lead, founder's associate, or strategic analyst. You've built internal tools and automations. You've managed complex multi-stakeholder processes. We care about your ability to independently model systems and act on what you see --- not your company logos. * **Who this isn't for.** This role is wrong if you need extensive direction before acting. It's wrong if "that's not my job" is part of your vocabulary. It's wrong if you're optimizing for a two-year stint on your resume before moving to a brand-name company. You'll thrive here if you want to build something that matters, work directly with the CEO, and own the operational engine of a company that's genuinely different. **How We Evaluate** 1. **Written artifact.** Something you've written or built that shows systems thinking --- a process doc, an automation, an analysis. 2. **Video screen.** How you think about operational complexity and prioritization. 3. **Conversation with the founder.** Chemistry and alignment. Can you model the system? 4. **Paid work trial.** 1-2 weeks embedded in AIOS operations. Real work, real tools, real output. **Compensation \& Ownership** * **Total first-year comp: $250,000 -- $350,000** (base + equity + profit sharing). * **Base:** $150,000 -- $200,000. * **Equity:** Profits Interest Units (PIUs) --- $0 strike price, Capital Gains tax treatment, actual ownership from day one. * **Profit sharing:** Annual free cash flow participation. Real cash every year. * **Liquidity:** Annual tender offer. No IPO required. * **Benefits:** 100% premium coverage. Unlimited PTO. Based in Santa Monica. In-office five days --- this role requires daily proximity to the CEO. Apply here: https://product.ai/join/ai-systems-associate Include a written artifact that shows how you think about systems --- an analysis, a process doc, something you built.