Director of Operations

Turn every idea worth doing into a plan, an owner and a date, and ship it.

Why this role exists

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.

Sales is closing. Marketing is scaling. The constraint on the next stage is the operating layer: our systems, our data, and how fast an idea becomes a shipped product.

Matt is the founder, the face and the content engine, with more good ideas than any team can ship. This role exists so every idea worth doing gets a plan, an owner and a date, and ships without Matt chasing it.

Matt is the visionary and you are the integrator: you run the operating side of the company with a roadmap, a scoreboard and a team you built. Grow with us and this seat becomes COO.

What you own

Integration and execution

Matt sends you a voice note with an idea. Within a day you come back with the plan: what it takes, who does it, what moves and the date it ships. Then it ships, and nothing else stalls along the way.

Turn every idea into a plan with an owner, a deadline and the trade-offs made visible.
Own the company project roadmap. Sequence it, reprioritize it and keep it moving.
Answer “yes, here is how,” not “do you know how much work that is?”
Run a weekly operations review so nothing ships late without warning.

Reporting and data

Reporting is the biggest gap today, so this is where you start. One set of numbers the whole company trusts, built on clean data and shown on dashboards leaders actually use.

Meet each leader, agree the numbers they need, and get them built.
Direct the data engineer: what to build, how it should work and by when.
Decide what goes on every dashboard. Define metrics only as far as we need to move.
Make failure visible. If data breaks, someone knows the same day.

Revenue operations

You work shoulder to shoulder with the Head of Sales as one unit. Every step from first click to booked call to cash collected runs on systems you own and keeps getting better.

Own the CRM, booking funnel and workflows. HubSpot stays the single source of truth.
Run HubSpot, Typeform, Zapier and integrations through the automation specialist you lead.
Own attribution with marketing: which channels produce buyers, not just calls.
Build a clean handoff from signed agreement into delivery.

Matt AI and product

Matt AI is our AI product, built from Matt's methodology. It is a revenue driver, a lead source and a window into what founders actually ask. You scope it, own the plan and get it to market.

Scope the V1 with Matt and set the launch date.
Ship it, then iterate fast. Fix what breaks and keep moving.
Turn what founders ask Matt AI into insight for product, sales and content.
Work with the Head of Customer Success on how it lands inside delivery.

Team and systems

You build the team that builds the systems, and you make the whole company more AI-enabled every quarter. Over time your scope grows into coaching and delivery operations, on the path to COO.

Hire, run and, when needed, exit the data, automation and development seats.
Bring AI and automation into every team. Show us what we no longer need to do by hand.
Write the playbooks so every seat is replaceable, including yours.
Grow into delivery operations: course completion, upgrades and the systems behind them.

Who you work with

Matt Gray, CEO. Vision, content, brand, demand and Edge. The roadmap and the biggest bets.
General Manager. The operating rhythm and the company scorecard. You bring the roadmap and the trusted numbers it runs on.
Chief of Staff. Operating rhythm, hiring and special projects.
Head of Sales. Pipeline, closers, setters and cash collected. You run sales operations and the numbers behind them together.
Head of Customer Success. Founder results and renewals. Delivery systems and the handoff from sale to kickoff.
Marketing. Attribution and funnels.

Who you run:

Data engineer. Data, payment systems and the database.
Automation specialist. HubSpot, Typeform, Zapier and integrations.
Developers and contractors. Product builds, including Matt AI.

The scorecard

You're measured on outcomes, not activity. Final numbers get set with Matt in your first 30 days.

Projects shipped on the committed date. Whether the plan is real.
Idea to dated plan. How fast Matt's ideas become something we can ship.
Trusted company scoreboard. One set of numbers every leader uses without double-checking.
Matt AI in market. V1 live, then usage, leads and revenue.
Data accuracy and system uptime. Whether anything is failing silently.
Hours automated. AI leverage across the company, quarter on quarter.
Projects needing Matt to unblock. Whether the seat is working. Trending to zero.
Team performance. Data, automation and dev seats filled and hitting their dates.

Your first 90 days

Days 1-30: Understand

Sit in sales, delivery and marketing meetings. Map every system we run and who owns it. Agree with each leader the numbers they need and get the first trusted dashboard live. Hire the automation specialist. Lock your scorecard numbers with Matt.

Days 31-60: Install

Move HubSpot and workflows to the automation specialist so the data engineer can focus on data. Stand up the weekly scoreboard used at every Level 10. Scope the Matt AI V1 with Matt and set the launch date. Put your roadmap and hiring plan in front of Matt.

Days 61-90: Run

Get Matt AI into market. Run the weekly operations review and the roadmap without Matt in the room. The bar at day 90: Matt sends one voice note and knows it will ship, on a date, without chasing anyone.

Who you are

You've run operations or revenue operations in a fast-moving, founder-led business, ideally high-ticket education, coaching, info-product or creator brands. You've led technical people without being the developer. You've shipped systems and products on deadlines. You use AI daily and have already rebuilt at least one process around it.

You'll do well here if:

You're an integrator. You turn ideas into plans with owners and dates, and you make them happen.
You're technical, but not a developer. You understand CRMs, automation, data and AI well enough to scope the work and lead the people who build it.
You're AI-native. You bring us things we didn't ask for: “I built this, and it saves us ten hours a week.”
You're fast and practical. You know when to build it right and when to ship it now and fix it next week.
You're curious, with integrity. If something looks wrong, you can't leave it alone until you know why.

This isn't for you if:

You need approvals, committees and long timelines.
You'd rather write the code than lead the build.
Your first answer is “do you know how much work that is?”
You need every definition settled before anything ships.
You need Matt to chase the deadline.

Unusual backgrounds welcome. A founder's right hand at an info-product brand, an agency operator, a sales rep who became the best ops hire their company ever made: if you've taken ideas from a voice note to a shipped system, we want to talk.

How we operate

Founder OS is built on freedom, community, creativity, and simplicity. Our values are how we operate, make decisions, give feedback, and hold each other accountable.

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.

The engagement

Type. Independent contractor, under a services agreement. You handle your own taxes and benefits.
Pay. $9,500 to $21,500 a month, plus performance pay tied to the projects you own: trusted reporting, Matt AI in market and the roadmap shipped on the dates you commit to.
Where and when. Fully remote. You set your own hours and methods. We book leadership meetings together, on US Eastern time.
Your setup. Your own equipment and tools. You invoice monthly, and you're free to work with other clients.

How to apply

Apply below with a short Loom: a project you owned from idea to launch.

Application and scorecard screen. We score for ownership, operating history and AI fluency.
Deep-dive interview on your track record against the five areas you'd own, project by project.
References. We call the people who worked for you, too.
Scope and 90-day plan, written together before you sign.

Founder OS runs on a simple belief: fear is the enemy of service, and systems are the path to freedom.

Founder OS is an equal opportunity company. We're building a diverse team of exceptional humans who dazzle founders every single day.

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