Head of Sales

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. The demand is real, and marketing is about to scale spend hard. Every dollar of it lands on the sales team.
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Matt is the founder, the face, and the content engine. He closes the biggest deals. This role exists so that everything else closes without him: a sales team that turns demand into cash collected, every month, at a number that climbs every quarter. This is an operator seat. You run the revenue side of the company the way a great GM runs a business: with a number, a scoreboard, and a team you built.

The Mandate

Five pillars. You own all five.

PILLAR 1  Cash Collected

You own the number. Not pipeline, not calls booked: cash in the bank. The first bar is $1M a month, held for three months straight. Then we raise it.

• Own monthly cash collected across every offer.
• Forecast weekly and land the month you called. No surprises.
• Set targets by rep, by source, and by offer, and hit them.
• Run the Edge pipeline so Matt's time goes only to the deals only he can close.

PILLAR 2  Team and Talent

You hire, manage, and when needed, exit the sales team: closers, setters, DM setters, and sales ops. You build ahead of the gap. When a rep isn't working, the replacement is already in conversation.

• Recruit and run the bench. Scorecards, call reviews, standards.
• Coach every rep weekly on recorded calls, not on feel.
• Keep a live recruiting pipeline so no seat sits empty.
• Make the people calls early, and protect the company while you do.

PILLAR 3  Process and Pipeline

A founder who applies should hear from us fast and have a sales conversation that feels like the product. You own the path from lead to signed contract, the CRM it runs on, and the conversion at every stage.

• Own HubSpot and pipeline hygiene. If it's not in the CRM, it didn't happen.
• Measure speed to lead in minutes, not hours.
• Write and maintain the scripts, objection handling, and playbooks.
• Build AI into the sales process so every rep sells like a team of three.

PILLAR 4  Sell What We Deliver

At high ticket, a bad close is worse than no close. Every promise made on a call lives in the contract or doesn't get made. You keep the pitch, the offer, and delivery saying the same thing, and you sell the right founder the right tier.

• Sell the offer as it is delivered. No side promises.
• Qualify hard. The right founder on the right tier, every time.
• Run a clean handoff to delivery on every closed deal.
• Feed objections and lost-deal reasons to marketing and product every week.

PILLAR 5  Renewals and Expansion

The easiest sale is the founder who already got a result. You partner with the Head of Product on renewals, on moving founders from Velocity to Edge, and on turning happy founders into referrals.

• Run renewal and ascension conversations alongside the delivery team.
• Build the referral motion so founders bring founders.
• Track expansion revenue as its own line.

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

Cash collected - The number, monthly, against target

Close rate- % of qualified calls that sign

Show rate - % of booked calls that happen

Speed to lead - Minutes from application to first contact

Cost per acquisition - Ad spend and team cost per signed founder, tracked with marketing

Forecast accuracy - Whether the month you called is the month we got

Refund rate on new deals - Whether we sold what delivery delivers

Rep ramp time - Days for a new closer to hit target

04

Who You Run

• Closers (Founder OS, Velocity, and Edge pipeline)
• Appointment setters and DM setters
• Sales operations (CRM, reporting, scheduling)
• Recruiters and partners who feed the bench

You work shoulder to shoulder with Devin (lead volume and quality, message to market), the Head of Product (clean handoff from closed deal to kickoff, renewals and ascension), and Matt (Edge and the biggest deals).

05

Your First 90 Days

DAYS 1-30  Understand

Listen to every recorded call from the last 60 days. Sit in on live calls. Shadow every setter and closer. Map the real funnel stage by stage, with conversion at each step. Audit HubSpot. Know who stays and who doesn't. Lock your scorecard numbers with Matt.

DAYS 31-60  Install

Make the people calls. Put your hiring plan in front of Matt and start filling seats. Rebuild the scripts and the handoff to delivery. Stand up the scoreboard: cash, close rate, show rate, speed to lead, forecast, all visible weekly.

DAYS 61-90  Run

Run sales without Matt in the room. Hold the weekly sales meeting, run the scorecard review, forecast the month and land it. The bar at day 90: Matt disappears for two weeks and the number still comes in.

06

Who This Person Is

You have built and run a high-ticket sales team, ideally selling five and six-figure offers in coaching, consulting, education, or professional services. You have hired, coached, and exited closers and setters. You have owned a cash number and hit it, month after month. You use AI daily and have already used it to make a sales team faster.

You are:

• A builder. You have the plan before anyone asks for it.
• Numbers-first. You know the funnel by stage, by rep, by day.
• A closer who coaches. You can take any call, and you'd rather make your team better at it.
• Decisive on people. You hire fast, coach hard, and act early when it isn't working.
• Honest in the room. You'd rather lose a deal than sell a founder something we don't deliver.

You are not:

• Someone who waits for a green light to fix what's broken.
• A top closer who wants the title without building the team.
• Someone who measures success in calls booked.
• Someone who needs Matt on the call to close.

Unusual backgrounds welcome. A top closer who built a team, a founder who ran their own sales floor, a sales leader from a high-ACV B2B company: if you have built a team that hits a cash number every month, we want to talk.

07

Compensation

Competitive base plus performance compensation tied to the numbers you own: cash collected, close rate, and refund rate. When the number comes in month after month, 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.

Values & 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.

09

How We Hire

1. Application and scorecard screen. We score for ownership, team-building history, and AI fluency.
2. Deep-dive interview. Your track record against the five pillars, number by number, plus how you'd coach one of our recorded calls.
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 revenue engine behind the operating system for founders, this is the seat.