What are the responsibilities and job description for the Director of Regulatory Operations, 2 Hour Learning (Remote) - $200,000/year USD position at Trilogy?
Elite regulatory navigators wanted: Be the person who makes the impossible possible.
This is the frontline role where operational excellence meets regulatory mastery. You'll secure the critical approvals that enable our schools to launch across all 50 states - translating complex legal frameworks into executable pathways. While others debate compliance theory, you'll be delivering the tangible permissions that power our national expansion.
You'll leverage cutting-edge AI tools to generate jurisdiction-specific research and automate filings with unprecedented speed, while applying your expert judgment to identify ambiguities, assess risks, and drive decisions. The intelligent systems you build will become the definitive source of truth for legal, operations, and executive teams - creating visibility where confusion once reigned.
This is not a support function. This is a builder role for execution-focused professionals who thrive on speed, ownership, and real-world impact. You won't just maintain compliance - you'll architect the frameworks that make our mission possible.
What You Will Be Doing
Secure and maintain the comprehensive legal authorizations enabling 2 Hour Learning to launch and operate schools nationwide by architecting, implementing, and executing technology-enhanced compliance systems designed for scalable growth.
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 They’re tearing down the outdated one-size-fits-all model and replacing it with AI-driven personalized learning that helps kids master academics in just two hours a day.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-Boise-DirectorofRegu
This is the frontline role where operational excellence meets regulatory mastery. You'll secure the critical approvals that enable our schools to launch across all 50 states - translating complex legal frameworks into executable pathways. While others debate compliance theory, you'll be delivering the tangible permissions that power our national expansion.
You'll leverage cutting-edge AI tools to generate jurisdiction-specific research and automate filings with unprecedented speed, while applying your expert judgment to identify ambiguities, assess risks, and drive decisions. The intelligent systems you build will become the definitive source of truth for legal, operations, and executive teams - creating visibility where confusion once reigned.
This is not a support function. This is a builder role for execution-focused professionals who thrive on speed, ownership, and real-world impact. You won't just maintain compliance - you'll architect the frameworks that make our mission possible.
What You Will Be Doing
- Deliver comprehensive legal research memos within 48 hours that transform fragmented regulatory requirements into actionable recommendations, leveraging AI acceleration for speed and accuracy.
- Construct and submit flawless state-specific filing packages, including exemption documentation, licensing applications, and entity filings - with zero dependency gaps.
- Implement and maintain real-time approval tracking dashboards that provide complete visibility, proactively escalate blockers, and trigger alerts well before critical deadlines.
- Resolve complex regulatory challenges including edge-case rejections and cross-jurisdictional conflicts, owning the entire approval process from submission to final authorization.
- Continuously enhance our AI and automation capabilities through rigorous testing, workflow optimization, and system updates that drive measurable improvements in speed and accuracy.
- Waiting for solutions from legal or product teams - you identify answers independently or build systems to generate them.
- Following outdated compliance protocols - you'll operate in a dynamic, AI-powered environment that demands continuous innovation.
- Managing post-submission corrections or quality issues - your work is thorough, accurate, and approved before deadlines, not after.
- Communicating status through disorganized email chains - you maintain transparent, audit-ready tracking systems accessible to all stakeholders.
- Treating compliance as a theoretical exercise - you own tangible outcomes that directly impact launch timelines and organizational success.
Secure and maintain the comprehensive legal authorizations enabling 2 Hour Learning to launch and operate schools nationwide by architecting, implementing, and executing technology-enhanced compliance systems designed for scalable growth.
Basic Requirements
- U.S.-based with authorization to work without sponsorship
- Commitment to travel 50-75% across U.S. jurisdictions
- Minimum 5 years of proven experience in compliance, permitting, legal operations, or multi-state regulatory management
- Demonstrated history of ownership and results in fast-paced, ambiguous regulatory environments
- Advanced proficiency with AI tools (ChatGPT, Claude, Perplexity) and low-code platforms (Retool, Airtable, Klair, Zapier)
- Exceptional execution velocity - consistently delivers critical filings and research within 48-hour timeframes without follow-up
- Superior communication precision - creates decision-ready memos, concise summaries, and documentation that withstands regulatory scrutiny
- Experience with AI prompt engineering, regulatory database navigation, or workflow design in compliance-intensive sectors
- Proven ability to anticipate and resolve complex regulatory challenges before they become operational blockers
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-Boise-DirectorofRegu
Salary : $200,000
