What are the responsibilities and job description for the Vice President of Compliance Operations, 2 Hour Learning (Remote) - $200,000/year USD position at Trilogy?
Ready to be the regulatory wizard who turns complex compliance puzzles into streamlined solutions?
This position transcends traditional compliance work—you'll be the strategic enabler who transforms regulatory roadblocks into launching pads for educational innovation. Your mission: orchestrate the intricate dance of multi-state approvals that breathe life into new educational institutions across America.
Harness cutting-edge AI technology, including sophisticated RAG systems, to craft jurisdiction-specific compliance strategies and accelerate regulatory processes at unprecedented speeds. Yet your human expertise remains irreplaceable—you're the critical decision-maker who navigates regulatory gray areas, identifies potential pitfalls, and drives resolution when others hit walls. You'll architect intelligent compliance ecosystems, maintain real-time operational dashboards, and ensure seamless information flow across legal, operational, and executive stakeholders.
This role demands a builder's mindset—someone who creates infrastructure rather than simply maintains it. You'll establish the regulatory foundation upon which our entire expansion strategy stands.
What You Will Be Doing
Establish and maintain the comprehensive regulatory framework enabling 2 Hour Learning's nationwide school deployment—through the creation, ownership, and execution of scalable, technology-enhanced compliance operations that support sustainable 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 They’re tearing down the outdated one-size-fits-all model and replacing it with AI-driven personalized learning that helps kids master academics in just two hours a day.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-Denver-VicePresidento
This position transcends traditional compliance work—you'll be the strategic enabler who transforms regulatory roadblocks into launching pads for educational innovation. Your mission: orchestrate the intricate dance of multi-state approvals that breathe life into new educational institutions across America.
Harness cutting-edge AI technology, including sophisticated RAG systems, to craft jurisdiction-specific compliance strategies and accelerate regulatory processes at unprecedented speeds. Yet your human expertise remains irreplaceable—you're the critical decision-maker who navigates regulatory gray areas, identifies potential pitfalls, and drives resolution when others hit walls. You'll architect intelligent compliance ecosystems, maintain real-time operational dashboards, and ensure seamless information flow across legal, operational, and executive stakeholders.
This role demands a builder's mindset—someone who creates infrastructure rather than simply maintains it. You'll establish the regulatory foundation upon which our entire expansion strategy stands.
What You Will Be Doing
- Generate comprehensive regulatory analysis reports using AI-powered research tools, converting complex multi-state requirements into clear actionable directives—all within 48-hour turnarounds.
- Orchestrate complete state-specific compliance packages, encompassing exemption requests, licensing applications, and corporate documentation—ensuring zero missed dependencies or incomplete submissions.
- Maintain dynamic compliance monitoring systems through custom-configured dashboards (Airtable, Klair, Retool), proactively identifying bottlenecks and triggering stakeholder notifications ahead of critical deadlines.
- Navigate complex regulatory challenges, resolve interstate compliance conflicts, and shepherd applications from initial submission through final approval certification.
- Optimize AI-driven compliance infrastructure through systematic testing, workflow enhancement, and performance improvements that boost both precision and processing velocity.
- Passively awaiting direction from legal or product teams—you're empowered to discover solutions independently and engineer systems that generate answers.
- Relying on outdated compliance frameworks or rigid procedural manuals—this position thrives on adaptive, technology-enhanced methodologies that evolve continuously.
- Scrambling to correct incomplete or substandard submissions—your deliverables are polished, comprehensive, and deadline-compliant from the outset.
- Communicating progress through fragmented email chains—all stakeholders access unified, real-time visibility through professionally maintained tracking systems.
- Treating compliance as theoretical exercise—you drive tangible results that directly influence launch schedules and organizational reputation.
Establish and maintain the comprehensive regulatory framework enabling 2 Hour Learning's nationwide school deployment—through the creation, ownership, and execution of scalable, technology-enhanced compliance operations that support sustainable growth.
Basic Requirements
- U.S.-based professional with unrestricted work authorization
- Comfortable with extensive travel commitments (50–75%) across diverse U.S. markets
- Minimum 5 years of specialized experience in compliance management, regulatory permitting, legal operations, or multi-jurisdictional business development
- Proven success record managing complex deliverables in dynamic, high-uncertainty environments
- Proficient daily practitioner of AI platforms (ChatGPT, Claude, Perplexity) and automation tools (Retool, Airtable, Klair, Zapier)
- Exceptional execution velocity—consistently delivers research and filings within 48-hour windows while maintaining proactive communication standards
- Superior written communication skills—produces executive-ready analyses, concise status reports, and compliance documentation suitable for audit review
- Experience with AI prompt optimization, regulatory research platforms, or compliance workflow architecture in highly regulated sectors
- Demonstrated ability to anticipate and resolve uncommon regulatory challenges before they impact project timelines
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-VicePresidento
Salary : $200,000
