Head of Product, AI

Founder OS is building toward a $100M company on a simple model: founders pay us five and six figures, and we install a Content Operating System that grows their brand and their revenue. That operating system runs on AI: a library of AI systems and skills, and Matt AI, built on 44,000 pieces of Matt's content.
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Matt is the founder, the face, and the content engine. Almost everything he knows is already recorded, written, and systemized. This role exists to turn that into products founders use every day, and into leverage the whole company runs on. This is a builder seat with a business attached.

You run AI at Founder OS the way a great GM runs a business unit: with a roadmap, a scoreboard, and users who would be upset if it went away.

02

The Mandate

Four pillars. You own all four.

PILLAR 1  Matt AI

Matt AI is Matt in a founder's pocket: his frameworks, his voice, his judgment, every day. You own it end to end, as a product. Open the app, see where you are on the path, see what to do today, ask Matt anything. You ship it to every Founder OS founder first, then build it into a standalone product line.

• Own the Matt AI roadmap, build, and release cadence.
• Show working builds every week. Ship to founders every month.
• Design for daily use: the founder's stage, their daily inputs, and Matt AI in one place.
• Build it as a business unit with its own revenue line.

PILLAR 2  The Content Operating System

The product founders buy runs on AI systems and skills. You build and maintain that stack so the output sounds like the founder, gets better every month, and never breaks. The Head of Product decides what founders need. You make it real.

• Own the AI systems and skills library founders are delivered on.
• Version, test, and quality-check every skill before it ships.
• Measure output quality: voice match, edit rate, time saved.
• Pressure-test every new model and tool against one question: does this get a founder to a result faster?

PILLAR 3  Internal Leverage

Founder OS is an AI-first company. Every team should operate like a team of ten. Matt's calls, assets, and skills are already recorded and organized. You turn them into SOPs, training, and workflows the team runs without him.

• Build AI-first workflows across sales, marketing, delivery, and operations.
• Turn Matt's recorded work into playbooks and handoffs the team can run.
• Automate the repeatable work so people spend time where judgment pays.
• Raise the bar on AI fluency across the team. It's a standard here, not a specialty.

PILLAR 4  The Data Advantage

Our edge is data no tool, agency, or competitor has: 44,000 pieces of content and the layers of data behind every asset. You own how that data is captured, structured, and put to work across Matt AI, the skills, and our founder results.

• Own the knowledge base behind Matt AI and the skills.
• Capture every new call, asset, and founder result into it.
• Keep it clean, current, and secure.

03

The Scorecard

You are measured on outcomes, not activity. Final numbers get locked with Matt in your first 30 days. These are the bars we care about:

Metric & What it tells us

Matt AI daily active founders - Whether founders open it because it helps

Daily input completion - Whether the app is building the habits that drive results

Matt AI revenue - The standalone product line, once launched

Skill output quality - Voice match, and how much founders have to edit

Ship cadence - Working builds weekly, releases monthly

Hours saved per team member - Internal leverage, measured, not guessed

Founders per FSM - AI efficiency in delivery, on the path to 1:80

04

Who You Run

• Engineers, designers, and contractors you bring in to build Matt AI
• Skill builders who maintain the AI systems and skills library
• Automation and internal tooling

You work shoulder to shoulder with Matt (the vision and the voice behind Matt AI), the Head of Product (what founders need, and adoption in delivery), and every team lead who needs to move faster.

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Your First 90 Days

DAYS 1-30  Understand

Use everything. Run the Content Operating System on yourself. Go through every skill, every Matt AI conversation, every recorded call you can. Interview ten founders on what they use daily and what they ignore. Map the AI stack as it is today. Lock your scorecard numbers with Matt.

DAYS 31-60  Install

Ship the first Matt AI build to a pilot group of founders. Fix the three skills that matter most. Put your roadmap and hiring plan in front of Matt. Stand up the scoreboard.

DAYS 61-90  Run

Matt AI live for every founder. A weekly build review, a monthly release, and the internal leverage plan running across every team. The bar at day 90: founders open Matt AI because it helps, not because we told them to.

06

Who This Person Is

You have built and shipped AI products real people use every day, and you owned the product, not just the code. You have taken something from mockup to live users to revenue. You can build it yourself, and you know when to hire. You understand that the tech is the easy part. The product is the hard part.

You are:

• A product person first. You build what founders love, not what is technically interesting.
• A builder. You ship working software every week.
• Taste-driven. You know a great app experience when you see one, and you build to that bar.
• Numbers-first. You measure usage, quality, and time saved.
• Founder-minded. You want to build a business unit, not maintain a tool.

You are not:

• A researcher who wants to experiment without shipping.
• Someone who needs a full engineering team before they start.
• Someone who measures success in tools tried.
• Someone who treats design as decoration.

Unusual backgrounds welcome. A founder who built an AI product, a product lead at a consumer app, an engineer who ships like a designer: if you have built something people use every day, we want to talk.

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Compensation

Competitive base plus performance compensation tied to what you build: Matt AI adoption, Matt AI revenue, and the leverage you create across the team. When Matt AI wins, you get paid like an owner. We go deep on structure and numbers in the live conversation.

08

How We Operate

Founder OS is built on freedom, community, creativity, and simplicity. Our values aren’t words on a wall. They’re how we operate, make decisions, give feedback, and hold each other accountable.

Value & How it shows up

Insanely Simple - Complexity is the enemy of execution.

Extreme Ownership - Every decision starts with “What is best for the enterprise?”

Writing-First Culture - If it’s not written, it doesn’t exist. Clarity is kindness.

Obsess Over Quality - We are tastemakers. Every touchpoint is a chance to dazzle.

All-In Mindset - The founder’s success is our success.

Elevated Design - Design is strategy. Taste is our competitive advantage.

Dazzle Founders - We treat founders like best friends and go the extra mile.

Relentless Velocity - We move quickly toward a common, specific goal.

Solutions, Not Problems - Never just bring a problem. Always bring a solution.

Above all, we are one team building one company.

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How We Hire

1. Application and scorecard screen. We score for ownership, shipping history, and product taste.
2. Deep-dive interview. Walk us through what you've built: live demos, usage numbers, what you'd change.
3. References. We call the people who worked for you, not just the people you worked for.
4. Offer and 90-day plan. We co-write it before you sign, so day one has no ambiguity.

Founder OS runs on a simple belief: fear is the enemy of service, and systems are the path to freedom. If you want to build the AI behind the operating system for founders, this is the seat.

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