What are the responsibilities and job description for the Head of Compliance Operations, 2 Hour Learning (Remote) - $200,000/year USD position at Crossover?
A law degree is not required — but you must be the person Legal turns to when they need answers.
This role is not centered on policy development. It is centered on authorization. You will be responsible for enabling new school launches by obtaining the regulatory clearances required for every campus to begin operating. You will own the full scope of work — from entity formation filings to license acquisition to securing specialized exemptions — that authorizes lawful operation in all 50 states.
AI-powered tools such as a RAG Bot will help you produce jurisdiction-specific guidance documents and process filings faster than ever, but you remain the critical reviewer who identifies ambiguity, surfaces red and yellow risks, escalates obstacles, and drives decision-making. While strategy discussions continue, you will be delivering outcomes. You will test and optimize intelligent workflows, update live tracking systems, and ensure nothing is overlooked. The infrastructure you create will serve as the authoritative reference for legal, operations, and leadership.
This is not a support function. It is a frontline execution role — demanding velocity, accountability, and applied regulatory expertise. You will not simply maintain existing operations. You will architect the foundation.
What You Will Be Doing
Obtain and uphold the regulatory authorizations required for 2 Hour Learning to launch and operate educational institutions nationwide — by building, managing, and executing technology-driven compliance frameworks that function 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 They’re tearing down the outdated one-size-fits-all model and replacing it with AI-driven personalized learning that helps kids master academics in just two hours a day.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-HeadofComplian1
This role is not centered on policy development. It is centered on authorization. You will be responsible for enabling new school launches by obtaining the regulatory clearances required for every campus to begin operating. You will own the full scope of work — from entity formation filings to license acquisition to securing specialized exemptions — that authorizes lawful operation in all 50 states.
AI-powered tools such as a RAG Bot will help you produce jurisdiction-specific guidance documents and process filings faster than ever, but you remain the critical reviewer who identifies ambiguity, surfaces red and yellow risks, escalates obstacles, and drives decision-making. While strategy discussions continue, you will be delivering outcomes. You will test and optimize intelligent workflows, update live tracking systems, and ensure nothing is overlooked. The infrastructure you create will serve as the authoritative reference for legal, operations, and leadership.
This is not a support function. It is a frontline execution role — demanding velocity, accountability, and applied regulatory expertise. You will not simply maintain existing operations. You will architect the foundation.
What You Will Be Doing
- Produce AI-enhanced legal research briefs that convert complex, fragmented regulatory structures into actionable go/no-go guidance — delivered within 48 hours.
- Prepare and file jurisdiction-specific submission packages — exemption requests, licensing documentation, and legal entity records — ensuring all dependencies are satisfied.
- Monitor every approval status in real time via dashboards you manage (such as Airtable, Klair, Retool), flagging obstacles and setting automated alerts ahead of key deadlines.
- Resolve edge-case denials, navigate multi-state discrepancies, and take full ownership of the compliance endgame — from initial submission through final approval signature.
- Iteratively improve the AI and automation infrastructure by evaluating outputs, designing new workflows, and deploying updates that enhance precision and turnaround time.
- Waiting for legal or product teams to supply answers — you are expected to uncover them independently or engineer the system that does.
- Relying on static checklists or legacy compliance manuals — this position is adaptive, AI-augmented, and in continuous evolution.
- Performing retroactive corrections or remedying incomplete filings — your submissions are accurate, comprehensive, and finalized ahead of deadlines, not in response to them.
- Communicating status updates through email chains — all stakeholders view the same live, audit-compliant tracker you maintain.
- Treating compliance as a theoretical function — you are accountable for real-world results that directly affect launch timelines and public operations.
Obtain and uphold the regulatory authorizations required for 2 Hour Learning to launch and operate educational institutions nationwide — by building, managing, and executing technology-driven compliance frameworks that function at scale.
Basic Requirements
- Located in the U.S. with work authorization that does not require sponsorship
- Available to travel 50–75% of the time to U.S. jurisdictions
- 5 years of experience in compliance, permitting, legal operations, or multi-state regulatory environments
- Proven history of driving outcomes in high-velocity, ambiguous settings
- Active daily user of AI platforms (such as ChatGPT, Claude, Perplexity) and low-code tools (such as Retool, Airtable, Klair, Zapier)
- Rapid executor — completes filings or research within 48 hours, follows through without external reminders
- Clear, structured communicator — produces decision-ready briefings, succinct summaries, and audit-ready documentation
- Experience with AI prompt engineering, regulatory research databases, or workflow design in compliance-intensive settings
- History of independently identifying and resolving unusual regulatory challenges
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-HeadofComplian1
Salary : $200,000
