Overview
Head of Compliance & Permitting, 2 Hour Learning (Remote) - $200,000 / year USD. Join to apply for this role at Trilogy. 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.
What You’ll 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from legal or product teams—you\'re the proactive solution-finder who builds the systems needed for successFollowing outdated compliance protocols—your approach will be dynamic, AI-powered, and continuously evolvingConducting after-the-fact corrections or cleanup—your work meets quality standards the first time and beats deadlines consistentlyCommunicating progress through scattered email chains—you\'ll maintain transparent, real-time dashboards accessible to all stakeholdersTreating compliance as a theoretical exercise—your work directly impacts launch timelines and organizational visibilityHead 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 sponsorshipAbility to travel extensively (50-75% of time) across multiple U.S. jurisdictionsMinimum 5 years of professional experience in compliance management, permitting processes, legal operations, or multi-state regulatory navigationProven ability to deliver results in fast-paced environments with significant ambiguityAdvanced 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 promptingSuperior communication skills—capable of creating decision-ready documentation, concise summaries, and compliance tracking systems that withstand audit scrutinyNice-to-have Requirements
Experience with AI prompt engineering, specialized regulatory database navigation, or workflow design in highly regulated industriesDemonstrated history of identifying and resolving complex regulatory edge cases before they become operational barriersAbout 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.
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.
Seniority level
DirectorEmployment type
Full-timeJob function
Legal, Engineering, and Project ManagementIndustries
ConstructionLegal ServicesPublic Policy OfficesMaryland, United States $165,000.00-$175,000.00 2 weeks ago
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