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Head of Compliance & Permitting, 2 Hour Learning (Remote) - $200,000/year USD
Head of Compliance & Permitting, 2 Hour Learning (Remote) - $200,000/year USDTrilogy • Washington, DC, United States
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Head of Compliance & Permitting, 2 Hour Learning (Remote) - $200,000 / year USD

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

Trilogy • Washington, DC, United States
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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 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  • Following outdated compliance protocols—your approach will be dynamic, AI-powered, and continuously evolving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

    • 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 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

  • Director

    • Employment type

  • Full-time

    • Job function

  • Legal, Engineering, and Project Management

    • Industries

  • Construction
  • Legal Services
  • Public Policy Offices

    • Maryland, United States $165,000.00-$175,000.00 2 weeks ago

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    Head Of Compliance • Washington, DC, United States