Head of Compliance & Permitting, 2 Hour Learning (Remote) - $200,000/year USD - Trilogy : Job Details

Head of Compliance & Permitting, 2 Hour Learning (Remote) - $200,000/year USD

This range is provided by Trilogy. Your actual pay will be based on your skills and experience — talk with your recruiter to learn more.

Base pay range

$100.00/hr - $100.00/hr

Become the regulatory pathfinder who transforms legal obstacles into launch opportunities. This position focuses on creating possibilities in education by navigating the regulatory landscape across all 50 states to secure approvals that enable new campuses to operate.

Equipped with cutting-edge AI tools and regulatory expertise, you will help revolutionize how compliance work happens. You will identify ambiguities, evaluate risk, and support decision-making when challenges arise, with our AI systems acting as trusted sources of truth for legal, operations, and leadership teams.

This role requires a builder's mindset—creating solutions, not just maintaining processes. You'll need decisiveness, ownership, and the ability to navigate complex regulatory environments with confidence. You will redesign the roadmap for maximum efficiency and scalability.

What You Will Be Doing

• Produce comprehensive legal research memos within 48-hour windows, translating regulatory frameworks into actionable recommendations using AI-enhanced tools
• Craft and submit flawless state-specific compliance packages including exemption documentation, licensing applications, and entity paperwork with zero gaps
• Develop and maintain real-time approval tracking systems through platforms like Airtable, Klair, or Retool, with proactive escalation protocols for potential roadblocks
• Resolve complex regulatory challenges and exceptions, taking full ownership from initial submission through final approval
• Enhance AI and automation infrastructure by testing, refining, and implementing workflow improvements to increase accuracy and efficiency

What You Won't Be Doing

• Passively awaiting direction from legal or product teams—be the proactive solution-finder who builds the systems needed for success
• Following outdated compliance protocols—your approach will be dynamic, AI-powered, and continuously evolving
• Conducting after-the-fact corrections or cleanup—your work meets quality standards the first time and beats deadlines
• Communicating progress through scattered email chains—maintain transparent, real-time dashboards accessible to all stakeholders
• Treating compliance as a theoretical exercise—your work directly impacts launch timelines and organizational visibility

Head Of Compliance & Permitting Key Responsibilities

Design, implement, and manage technology-enhanced compliance systems that secure and maintain the necessary legal authorizations for 2 Hour Learning to launch and operate educational facilities across the United States at scale.

Basic Requirements

• U.S.-based candidate with authorization to work without requiring sponsorship
• Ability to travel extensively (50-75% of time) across multiple U.S. jurisdictions
• Minimum 5 years of professional experience in compliance management, permitting processes, legal operations, or multi-state regulatory navigation
• Proven ability to deliver results in fast-paced environments with significant ambiguity
• Advanced proficiency with AI tools (ChatGPT, Claude, Perplexity) and experience with low-code platforms (Retool, Airtable, Klair, Zapier)
• Exceptional execution speed—consistently delivering research and filings within 48-hour timeframes without follow-up prompting
• Superior communication skills—capable of creating decision-ready documentation, concise summaries, and compliance tracking systems that withstand audit scrutiny

Nice-to-have Requirements

• Experience with AI prompt engineering, regulatory database navigation, or workflow design in highly regulated industries
• History of identifying and resolving complex regulatory edge cases before they become operational barriers

About 2 Hour Learning

Education is broken, but 2 Hour Learning is proving it doesn't have to be. They're leveraging AI-driven personalized learning to help students master academics in just two hours a day.

Students are ranked highly nationally, and the organization emphasizes talent and performance. They offer a dynamic, on-campus and remote-friendly environment where innovators, educators, and AI specialists can contribute to improving education.

2 Hour Learning is reprogramming learning for the AI era.

Here's how they're addressing the challenge. If you're interested, click Apply to learn more. They look forward to meeting you!

Working with us

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

Crossover Job Code: LJ-5678-US-Connecti-HeadofComplian

Seniority levelDirectorEmployment typeFull-timeJob functionLegal, Engineering, and Project ManagementIndustriesConstruction, Legal Services, and Public Policy Offices

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