Licensing & Permitting Director, 2 Hour Learning (Remote)

Master the Regulatory Maze That Others Can't Navigate

This isn't just compliance work—it's mission-critical infrastructure. As our Licensing & Permitting Director, you'll secure the regulatory foundation that enables our schools to launch across all 50 states. While others get lost in regulatory complexity, you create clarity and deliver outcomes.

You'll leverage cutting-edge AI tools to generate jurisdiction-specific analyses and automate filings with unprecedented speed, but your human judgment remains the critical element. You identify ambiguities, flag risks, escalate blockers, and drive decisions that matter. The intelligent systems you build become the single source of truth for legal, operations, and executive teams.

This frontline role demands exceptional speed, ownership, and regulatory judgment. You won't just maintain compliance—you'll architect the frameworks that make nationwide scale possible.

What You Will Be Doing

• Deliver AI-enhanced legal research memos that transform complex regulatory landscapes into actionable recommendations within 48-hour timeframes
• Construct and submit comprehensive state-specific filing packages—including exemption documentation, licensing applications, and legal entity filings—with zero dependency failures
• Maintain real-time approval tracking through self-configured dashboard systems, proactively escalating blockers and triggering alerts before deadlines approach
• Resolve complex regulatory rejections, reconcile interstate compliance conflicts, and own end-to-end approval processes from submission to final authorization
• Continuously optimize our AI and automation infrastructure by validating outputs, engineering workflows, and implementing updates that enhance accuracy and efficiency
  
  

What You Won’t Be Doing

• Passively waiting for solutions from legal or product teams—you proactively find answers or build systems to generate them
• Following outdated compliance protocols—your approach is dynamic, AI-powered, and constantly evolving
• Conducting post-deadline remediation work—your submissions are thorough, precise, and approved before deadlines expire
• Managing status updates through disorganized communication channels—you maintain transparent, audit-ready tracking systems accessible to all stakeholders
• Treating compliance as a theoretical exercise—you deliver concrete outcomes that directly impact launch timelines and organizational visibility
  
  

Licensing & Permitting Director Key Responsibilities

Establish and maintain the comprehensive legal authorization framework that enables 2 Hour Learning to launch and operate schools nationwide—by designing, implementing, and executing technology-enhanced compliance systems engineered for scalability.

Basic Requirements

• U.S.-based and authorized to work without sponsorship requirements
• Prepared to travel 50-75% of the time across multiple U.S. jurisdictions
• Minimum 5 years of experience in compliance, permitting, legal operations, or multi-state regulatory management
• Proven history of delivering results in fast-paced environments with regulatory ambiguity
• Proficient daily user of AI platforms (ChatGPT, Claude, Perplexity) and low-code development tools (Retool, Airtable, Klair, Zapier)
• Exceptional execution speed—consistently delivers research and filings within 48 hours and completes tasks without follow-up prompting
• Superior communication precision—produces decision-ready memoranda, concise summaries, and audit-compliant tracking documentation
  
  

Nice-to-have Requirements

• Experience with AI prompt engineering, regulatory database management, or workflow design in highly-regulated environments
• Demonstrated ability to identify and resolve complex regulatory challenges before they impact operations
  
  

About 2 Hour Learning

Education is broken, but 2 Hour Learning is proving it doesn’t have to be. They’re tearing down the outdated one-size-fits-all model and replacing it with AI-driven personalized learning that helps kids master academics in just two hours a day.

With students consistently ranking in the top 1-2% nationally and the top 20% achieving an astonishing 6.5x growth, they’re proving that smarter learning is possible. At 2 Hour Learning, it’s talent and performance that matter.

They offer a dynamic, on-campus and remote-friendly environment where innovators, educators, and AI specialists can be a part of fixing a broken school system.

2 Hour Learning is reprogramming learning for the AI era.

Here’s How They’re Fixing It.

There is so much to cover for this exciting role, and space here is limited. Hit the Apply button if you found this interesting and want to learn more. We look forward to meeting you!

Working with us

This is a full-time (40 hours per week), long-term position. The position is immediately available and requires entering into an independent contractor agreement with Crossover as a Contractor of Record. The compensation level for this role is $100 USD/hour, which equates to $200,000 USD/year assuming 40 hours per week and 50 weeks per year. The payment period is weekly. Consult www.crossover.com/help-and-faqs for more details on this topic.

Crossover Job Code: LJ-5678-US-CapeCora-Licensing&Perm