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

Overview

Head of Compliance & Permitting, 2 Hour Learning (Remote) — $200,000/year USD. Become the regulatory pathfinder who transforms legal obstacles into launch opportunities. This role focuses on creating possibilities by charting the regulatory landscape across all 50 states, securing critical approvals to launch educational campuses across the United States.

Equipped with AI tools and regulatory instincts, you'll help revolutionize how compliance work happens, while identifying ambiguities, evaluating risk, and driving decision-making. You will redesign processes for maximum efficiency and scalability, acting as the trusted source of truth for legal, operations, and leadership teams.

This is a builder role requiring decisiveness, ownership, and confidence navigating complex regulatory environments.

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 dependency 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, owning the compliance journey from initial submission through final approval
• Enhance our AI and automation infrastructure by testing, refining, and implementing workflow improvements that drive 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• Following outdated compliance protocols—your approach will be dynamic, AI-powered, and continuously evolving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 successfully launch and operate educational facilities throughout 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, specialized regulatory database navigation, or workflow design in highly regulated industries
• Demonstrated 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 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 a 6.5x growth, they're proving that smarter learning is possible. At 2 Hour Learning, talent and performance matter. They offer a dynamic, on-campus and remote-friendly environment where innovators, educators, and AI specialists can be part of fixing a broken school system. 2 Hour Learning is reprogramming learning for the AI era.

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. For details, see www.crossover.com/help-and-faqs.

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