Build and run the systems that capture data, and keep that data present and accurate.
01
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.
Every lead, call, payment, commission and Matt AI answer runs on data. Department heads bring the need. This role builds and runs the systems that capture it, and keeps it present and accurate.
Business decisions stay with the people who own the outcome. You own how it gets built.
02
What you own
CRM and email
HubSpot, or our current CRM: objects, pipelines, properties, workflows and permissions. Plus the email system inside it: sequences, automations and deliverability.
- Every record captured complete and deduped.
- Opens and clicks captured raw for Marketing.
- Delivered rate, send volume and suppression held to our deliverability spec.
Booking funnel
Webflow forms, Typeform, iClosed booking and routing, Aloware, SMS and email reminders, Zoom, the pixel, server-side events and UTMs.
- Every lead, click and booking captured with its source.
- Signals reach Meta, deduped.
Money systems
Turnstile is our deal enforcement system. Every deal and payment plan is built from approved terms, and anything outside them goes to approval. Plus payment links and plans, agreements, ingestion from Stripe, Whop, Mercury and HubSpot, the AR engine and the commission engine.
- Every payment tied to a deal.
- Every commission calculated to the written plan.
- Every Turnstile action shows the rule it followed.
AI systems
Matt AI (formerly ARIA) and the skills sync between GitHub and Google Drive.
- Matt AI reads Matt's content on every platform, with its metrics and attribution.
- The knowledge base stays fresh, and answers stay accurate.
- Skills stay in sync.
Access
SSO and SCIM provisioning by role.
- Access matches the role on every start and exit.
Underneath all five
Raw tables in Supabase, queryable in SQL and validated against the source systems. That's the source of truth. Owners build on it freely.
03
Who you work with
- General Manager. Sets company priorities and decides what leadership needs to see.
- Department heads. Head of Sales, the Paid Media Manager, Head of Customer Success and Georgi in finance each write the definition of what they need captured. You build to it.
- Matt Gray, CEO. Decides what Matt AI is and who it serves.
- Approvals. Exceptions inside your systems, like custom deal terms in Turnstile, go to the Head of Sales first, and to the General Manager when the Head of Sales is unavailable. Either can approve.
04
The scorecard
You're measured on the systems. The numbers they carry belong to their owners.
- Accuracy. Raw tables reconcile to the source systems on every validation run.
- Health. Uptime, error rate and time to fix, published every week.
- Traceability. Every Turnstile action, AR match and commission shows the rule it followed.
- Exceptions. Every input outside approved parameters routed or returned to its owner.
- Email. Delivered rate 99% or better, daily volume within 10% of baseline, hard bounces suppressed the same day, unsubscribes honored within 2 days.
- Matt AI. Uptime, errors, login and access, answer accuracy and knowledge base freshness.
- Access. Provisioned to the role on every start and exit.
- Records. Current with every build.
- Weekly updates. Monday and Friday updates posted on time, and every meeting on time with an agenda.
05
Your first 90 days
Days 1-30: Understand
Map every system, integration and login. Get iClosed, HubSpot and SMS sharing data correctly. Capture every booked call with its stage, status, setter and source.
Days 31-60: Install
Turnstile live: every new deal and payment plan comes from approved terms. Matt AI reads Matt's content on every platform.
Days 61-90: Run
Every raw table reconciles on every run. The weekly health report catches errors before anyone reports them.
06
Who you are
You've built and run the systems behind a sales team: the CRM, the integrations, the payments and the data underneath. You write code when a no-code tool runs out, and you use AI every day.
You'll do well here if:
- A number that doesn't reconcile bothers you until it does.
- You put the fix in at the root, so it stays fixed.
- If it only lives in your head, you don't call it done.
- You build to a written definition, and you send it back when it's unclear.
07
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.
08
The engagement
- Type. Independent contractor, under a services agreement. You handle your own taxes and benefits.
- Pay. $8,700 to $18,800 a month.
- Where and when. Fully remote. You set your own hours and methods. Your end-of-day handoff note and the Monday and Friday updates carry the work across time zones.
- Your setup. Your own equipment and tools. You invoice monthly, and you're free to work with other clients.
09
How to apply
Apply below with a short Loom walking through a system you built: what broke and how you fixed it.
- Application and portfolio screen.
- Technical deep dive on a system you built.
- Paid test project: a short, real problem from our stack.
- 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.
