What are the responsibilities and job description for the Head of Compliance & Permitting, 2 Hour Learning (Remote) - $200,000/year USD position at Trilogy?
Become the regulatory pathfinder who transforms legal obstacles into launch opportunities.
This position isn't about enforcing rules—it's about creating possibilities. As our compliance navigator, you'll chart the course that allows new educational campuses to open their doors across America. You'll master the regulatory landscape of all 50 states, securing the critical approvals that transform plans into operational reality.
Equipped with cutting-edge AI tools and your own regulatory instincts, you'll revolutionize how compliance work happens. While the RAG Bot generates jurisdiction-specific documentation at unprecedented speed, you'll be the crucial human element who identifies ambiguities, evaluates risk levels, and drives decision-making when challenges arise. Your intelligent systems will become the trusted source of truth that legal, operations, and leadership teams rely on daily.
This role demands a builder's mindset—someone who creates solutions rather than just maintaining processes. You'll need decisiveness, ownership, and the ability to navigate complex regulatory environments with confidence. You won't just follow the existing roadmap; you'll redesign it for maximum efficiency and scalability.
What You Will Be Doing
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
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 They’re tearing down the outdated one-size-fits-all model and replacing it with AI-driven personalized learning that helps kids master academics in just two hours a day.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.
Here’s How They’re Fixing It.
There is so much to cover for this exciting role, and space here is limited. Hit the Apply button if you found this interesting and want to learn more. We look forward to meeting you!
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-Denver-HeadofComplian
This position isn't about enforcing rules—it's about creating possibilities. As our compliance navigator, you'll chart the course that allows new educational campuses to open their doors across America. You'll master the regulatory landscape of all 50 states, securing the critical approvals that transform plans into operational reality.
Equipped with cutting-edge AI tools and your own regulatory instincts, you'll revolutionize how compliance work happens. While the RAG Bot generates jurisdiction-specific documentation at unprecedented speed, you'll be the crucial human element who identifies ambiguities, evaluates risk levels, and drives decision-making when challenges arise. Your intelligent systems will become the trusted source of truth that legal, operations, and leadership teams rely on daily.
This role demands a builder's mindset—someone who creates solutions rather than just maintaining processes. You'll need decisiveness, ownership, and the ability to navigate complex regulatory environments with confidence. You won't just follow the existing roadmap; you'll redesign it for maximum efficiency and scalability.
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
- 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
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
- 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
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.
Here’s How They’re Fixing It.
There is so much to cover for this exciting role, and space here is limited. Hit the Apply button if you found this interesting and want to learn more. We look forward to meeting you!
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-Denver-HeadofComplian
Salary : $200,000
