Head of Compliance & Permitting $200,000 USD/year Pay is set based on global value, not the local market.
Most roles = hourly rate x 40 hrs x 50 weeks
Description
Think regulatory roadblocks are just part of the game? Think again.
We're looking for someone who turns "impossible" into "approved" — the person who clears the path for educational innovation across America. You'll be our regulatory navigator, transforming complex compliance landscapes into streamlined approval pipelines that fuel our nationwide expansion.
Armed with cutting-edge AI technology and your sharp regulatory instincts, you'll architect permission systems that work at lightning speed. While others get bogged down in bureaucratic maze-running, you'll be building the express lanes. Your AI-powered research will cut through regulatory fog, your systematic approach will eliminate bottlenecks, and your proactive problem-solving will keep our growth trajectory on track.
This is where regulatory expertise meets technological innovation — where your ability to decode legal complexities becomes the engine that powers educational transformation nationwide.
What you will be doing
- Generate lightning-fast regulatory intelligence using AI-powered research tools, transforming complex legal landscapes into clear action plans within 48-hour turnarounds.
- Orchestrate multi-state filing campaigns with surgical precision — coordinating exemptions, licenses, and entity registrations without dropping a single requirement.
- Engineer real-time compliance monitoring systems using platforms like Airtable and Retool, creating transparency that keeps all stakeholders aligned and deadlines met.
- Navigate regulatory curveballs and cross-jurisdictional conflicts, becoming the go-to problem-solver when standard procedures hit unexpected walls.
- Evolve our AI compliance infrastructure by testing new workflows, optimizing automation sequences, and pushing the boundaries of what's possible in regulatory operations.
What you will NOT be doing
- Playing the waiting game for direction from other departments — you're the one who charts the course and finds the solutions.
- Wrestling with outdated processes or rigid compliance frameworks — your world is fluid, tech-enhanced, and built for rapid adaptation.
- Scrambling to fix last-minute filing disasters — your systems are designed for precision and your work hits the mark before crunch time.
- Drowning stakeholders in email updates — your dashboards tell the story in real-time, keeping everyone informed without inbox overload.
- Treating compliance as a theoretical exercise — every decision you make has direct impact on our ability to open doors and serve students.
Key responsibilities
Drive the regulatory engine that powers 2 Hour Learning's national expansion — by creating, managing, and optimizing technology-enhanced compliance systems that transform complex approval processes into predictable, scalable operations.
Candidate requirements
- U.S.-based with full work authorization (no sponsorship required)
- Ready for extensive travel (50–75%) to navigate jurisdictions firsthand
- 5+ years mastering compliance, permitting, or multi-state regulatory operations
- Proven ability to drive results in high-velocity, ambiguous environments
- Power user of AI platforms (ChatGPT, Claude, Perplexity) and automation tools (Retool, Airtable, Zapier)
- Speed demon who consistently delivers research and filings within 48-hour windows
- Communication craftsman who creates crystal-clear memos, summaries, and tracking systems
Nice to have
- Experience with AI prompt optimization, regulatory database navigation, or workflow design in compliance-intensive sectors
- History of identifying and resolving unusual regulatory challenges before they become roadblocks
Applying for a role? Here’s what to expect.
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Pass 
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