What are the responsibilities and job description for the Head of Compliance & Permitting, 2 Hour Learning (Remote) - $200,000/year USD position at Trilogy?
Regulatory Pathfinder Wanted: The Person Who Makes "Impossible" Launches Possible
This isn't about policy theory. It's about regulatory execution. You'll be the force that transforms legal barriers into launch runways, securing the complex web of approvals that enable our schools to open across all 50 states. From entity formations to license acquisitions to navigating exemption mazes, you own the mission-critical work that transforms regulatory challenges into operational reality.
You'll leverage cutting-edge AI tools to generate jurisdiction-specific analyses and accelerate filings, while applying the critical human judgment that spots ambiguities, flags risks, and drives decisions. While others debate hypotheticals, you deliver tangible outcomes. Your intelligent systems and dashboards will become the definitive source of truth for legal, operations, and executive leadership.
This is a frontline builder role that demands velocity, ownership, and sophisticated regulatory judgment. You won't just maintain compliance—you'll architect it.
What You Will Be Doing
Secure and maintain the comprehensive legal authorizations enabling 2 Hour Learning to launch and operate educational institutions nationwide—through the design, ownership, and execution of scalable, technology-driven compliance systems.
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 They’re tearing down the outdated one-size-fits-all model and replacing it with AI-driven personalized learning that helps kids master academics in just two hours a day.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-CapeCora-HeadofComplian
This isn't about policy theory. It's about regulatory execution. You'll be the force that transforms legal barriers into launch runways, securing the complex web of approvals that enable our schools to open across all 50 states. From entity formations to license acquisitions to navigating exemption mazes, you own the mission-critical work that transforms regulatory challenges into operational reality.
You'll leverage cutting-edge AI tools to generate jurisdiction-specific analyses and accelerate filings, while applying the critical human judgment that spots ambiguities, flags risks, and drives decisions. While others debate hypotheticals, you deliver tangible outcomes. Your intelligent systems and dashboards will become the definitive source of truth for legal, operations, and executive leadership.
This is a frontline builder role that demands velocity, ownership, and sophisticated regulatory judgment. You won't just maintain compliance—you'll architect it.
What You Will Be Doing
- Deliver AI-powered legal research memos that transform complex regulatory landscapes into actionable recommendations within 48-hour turnarounds
- Construct and submit comprehensive state-specific filing packages—including exemption documentation, licensing applications, and entity formation materials—with zero dependency gaps
- Maintain real-time approval tracking through self-configured dashboard systems (Airtable, Klair, Retool), with proactive escalation protocols for blockers and automated deadline alerts
- Resolve complex regulatory rejections, reconcile multi-state compliance conflicts, and drive approvals from submission to final authorization
- Continuously enhance our AI and automation infrastructure by validating outputs, engineering workflows, and implementing updates that drive precision and efficiency
- Depending on legal or product teams for solutions—you identify answers independently or build systems that deliver them
- Operating from static compliance protocols—your environment is dynamic, AI-enhanced, and continuously evolving
- Managing remediation work or correcting deficient filings—your deliverables are thorough, accurate, and completed ahead of deadlines
- Communicating status through fragmented email chains—all stakeholders access a centralized, audit-ready tracking system
- Treating compliance as theoretical—you drive concrete outcomes that directly impact launch timelines and market presence
Secure and maintain the comprehensive legal authorizations enabling 2 Hour Learning to launch and operate educational institutions nationwide—through the design, ownership, and execution of scalable, technology-driven compliance systems.
Basic Requirements
- U.S.-based with authorization to work without sponsorship
- Prepared for 50-75% travel across U.S. jurisdictions
- Minimum 5 years of experience in compliance management, regulatory permitting, legal operations, or multi-state business expansion
- Proven history of delivering results in fast-paced, ambiguous regulatory environments
- Advanced proficiency with AI platforms (ChatGPT, Claude, Perplexity) and low-code development tools (Retool, Airtable, Klair, Zapier)
- Execution-focused professional—consistently delivers research and filings within 48-hour windows and completes tasks without follow-up
- Exceptional communicator—produces decision-enabling memos, concise summaries, and documentation that withstands regulatory scrutiny
- Experience with AI prompt engineering, regulatory database management, or workflow design in compliance-intensive sectors
- Demonstrated ability to identify and resolve complex regulatory obstacles before they impact operations
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-CapeCora-HeadofComplian
Salary : $200,000
