Head of Compliance Operations, 2 Hour Learning (Remote) - $200,000/year USD
Trilogy
Date: 1 day ago
City: Centennial, CO
Salary:
$100
per hour
Contract type: Full time
Remote
You don't need a law degree... but you do need to be the person Legal calls when they're stuck.
This role isn't about policy. It's about permission. You'll be the one who makes it possible for new schools to open, securing the regulatory greenlights that power every campus launch. From entity filings to license approvals to edge-case exemptions, you will own the work that unlocks legal operation across all 50 states.
You'll use AI tools like a RAG Bot to generate jurisdiction-specific memos and automate filings in record time, but you're also the human in the loop who spots ambiguity, flags red/yellow risks, escalates blockers, and gets decisions made. While others debate strategy, you ship results. You'll test and refine intelligent workflows, push updates to live dashboards, and make sure nothing slips through the cracks. The systems you build will be the source of truth for legal, ops, and executive teams.
This isn't a support role. It's a frontline builder job — one that requires speed, ownership, and real-world regulatory judgment. You won't just keep the trains running. You'll lay the track.
What You Will Be Doing
Secure and maintain the legal approvals that allow 2 Hour Learning to launch and operate schools across the U.S. — by designing, owning, and executing tech-enabled compliance systems that work 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 They’re tearing down the outdated one-size-fits-all model and replacing it with AI-driven personalized learning that helps kids master academics in just two hours a day.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-Centenni-HeadofComplian1
This role isn't about policy. It's about permission. You'll be the one who makes it possible for new schools to open, securing the regulatory greenlights that power every campus launch. From entity filings to license approvals to edge-case exemptions, you will own the work that unlocks legal operation across all 50 states.
You'll use AI tools like a RAG Bot to generate jurisdiction-specific memos and automate filings in record time, but you're also the human in the loop who spots ambiguity, flags red/yellow risks, escalates blockers, and gets decisions made. While others debate strategy, you ship results. You'll test and refine intelligent workflows, push updates to live dashboards, and make sure nothing slips through the cracks. The systems you build will be the source of truth for legal, ops, and executive teams.
This isn't a support role. It's a frontline builder job — one that requires speed, ownership, and real-world regulatory judgment. You won't just keep the trains running. You'll lay the track.
What You Will Be Doing
- Deliver AI-accelerated legal research memos that translate fragmented regulatory frameworks into go/no-go recommendations — within 48 hours.
- Build and submit state-specific filing bundles — including exemption letters, licensing forms, and legal entity documentation — without missing a dependency.
- Track every approval in real time using dashboards you configure (e.g., Airtable, Klair, Retool), escalating blockers and triggering alerts before deadlines hit.
- Troubleshoot edge-case rejections, resolve cross-state conflicts, and own the final mile of compliance — from submission to signed-off approval.
- Continuously refine the AI and automation stack by testing outputs, designing workflows, and pushing updates that improve accuracy and speed.
- Waiting on legal or product to hand you answers — you're expected to find them or build the system that will.
- Working with static checklists or outdated compliance playbooks — this job is dynamic, AI-driven, and constantly evolving.
- Running backend rework or fixing sloppy filings — your work is clean, complete, and signed off before deadlines, not after.
- Reporting status via email threads — every stakeholder sees what you see in a live, audit-ready tracker.
- Managing compliance like an academic exercise — you own outcomes that impact launch dates and public visibility.
Secure and maintain the legal approvals that allow 2 Hour Learning to launch and operate schools across the U.S. — by designing, owning, and executing tech-enabled compliance systems that work at scale.
Basic Requirements
- Based in the U.S. and authorized to work without sponsorship
- Willing to travel 50–75% of the time across U.S. jurisdictions
- 5+ years in compliance, permitting, legal ops, or multi-state operations
- Demonstrated track record of owning outcomes in fast-moving, ambiguous domains
- Daily user of AI tools (e.g., ChatGPT, Claude, Perplexity) and low-code platforms (e.g., Retool, Airtable, Klair, Zapier)
- High-speed executor — delivers filings or research within 48 hours, closes loops without prompting
- Precision communicator — writes decision-ready memos, crisp summaries, and audit-proof trackers
- Familiarity with AI prompt engineering, regulatory databases, or designing workflows in compliance-heavy environments
- Track record of proactively spotting and solving edge-case regulatory 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-Centenni-HeadofComplian1
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