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

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

What You Will Be Doing

• Produce comprehensive legal research memos within 48-hour windows, translating complex 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, taking full ownership of the compliance journey from initial submission through final approval
• Enhance our AI and automation infrastructure by testing, refining, and implementing workflow improvements that drive increased accuracy and efficiency

What You Won't Be Doing

• Passively awaiting direction from legal or product teams—you\'re 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• Following outdated compliance protocols—your approach will be dynamic, AI-powered, and continuously evolving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 consistently
• Communicating progress through scattered email chains—you\'ll maintain transparent, real-time dashboards accessible to all stakeholders
• Treating compliance as a theoretical exercise—your work directly impacts launch timelines and organizational visibility

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. 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.

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-Cook-HeadofComplian

Job metadata

• Seniority level: Director
• Employment type: Full-time
• Job function: Legal, Engineering, and Project Management
• Industries: Construction, Legal Services, and Public Policy Offices

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