Chief Operating Officer (COO)

Crawford Thomas Recruiting • Full-time • Celebration, FL, US • $150,000 - $200,000 / year • 23h ago

Chief Operating Officer (COO) – Media & AI SaaS Transition

Salary: $150,000 – $200,000 Base + Performance Bonus (10–20%)

Location: Orlando, FL (Onsite)

THE MISSION

To transform a high-performing, founder-led organization into a predictable, execution-driven enterprise. You are being hired to build a scalable operating company that functions independently of the founder, making the business highly investable and ready for a strategic AI SaaS exit within 3–5 years.

What Success Looks Like (12–24 Months)

Founder Autonomy: The day-to-day business runs without the founder in the "middle."

Operational Maturity: The Marketing Agency division is metrics-driven, scaling toward $350k+ MRR.

Integrated Ecosystem: Events, media, coaching, and AI SaaS divisions operate as a unified, high-margin machine.

Exit Preparedness: Reporting and infrastructure are "due-diligence ready," moving from a private success to an institutional asset.

CORE OWNERSHIP AREAS

Strategic Execution: Translate visionary concepts into resourced, executable roadmaps. You own the weekly leadership cadence and the removal of cross-departmental friction.

Leadership & Culture: Directly lead and develop the "Second Layer" of management (Heads of Sales, Marketing, AI/Product, and Events). You are responsible for hiring, coaching, and—when necessary—upgrading talent.

AI / SaaS Scale-Up: Operationalize the AI division. You will track and optimize core SaaS metrics: MRR, Churn, LTV, and CAC to prepare for a potential spin-out.

Infrastructure & KPIs: Build the playbooks, SOPs, and dashboards that drive predictability. Partner with finance to improve margins and forecasting.

Institutional Readiness: Implement the documentation and reporting standards required for Private Equity or strategic buyers.

IDEAL CANDIDATE PROFILE

The "Scale-Up" Veteran: You have operated in the $10M–$30M revenue range and managed teams of 30–100+ people.

Hybrid Experience: You understand the unique nuances of Media, Education, and SaaS business models.

Founder Partner: You have a track record of working successfully with visionary founders, acting as the "steady hand" that operationalizes their ideas.

Systems Thinker: You don't just manage tasks; you build the systems that eliminate the need for manual management.

THIS IS NOT FOR YOU IF...

You come exclusively from a large corporate background and lack "startup grit."

You prefer to be a "mini-CEO" rather than an execution partner.

You avoid tough people decisions or high-accountability conflict.

You need a manual to operate rather than being the one who writes it.

90-DAY MILESTONES

Day 30: Complete operational diagnostic and build a trusted partnership with the founder.

Day 60: New leadership cadence in place; 20–30% of founder’s operational load successfully offloaded.

Day 90: Full ownership of execution and leadership meetings. A clear 24-month roadmap for exit-readiness is established.

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