What are the responsibilities and job description for the Head of Compliance & Permitting, 2 Hour Learning (Remote) - $200,000/year USD position at Crossover?
If you've led a construction or regulatory project for a school, hospital, or retail buildout and thought, "We could move faster without cutting corners," this role is worth your attention.
2 Hour Learning is scaling the fastest school model in the United States. Every new site depends on securing the right licenses, permits, and operational approvals—accurately and on schedule. You will determine what's needed, coordinate filings across jurisdictions, and ensure timely approvals. You'll leverage AI and automation tools, but you'll also engage directly with officials, follow up with contractors, and resolve edge cases that require human judgment.
This position is designed for someone who operates effectively under pressure and tight deadlines. You'll be part of a fast-moving organization with substantial resources and support, where both speed and precision are expected. You'll apply AI-enabled tools to streamline bureaucratic processes, reduce permitting cycles, and deliver outcomes rather than process documents.
If you're ready to be the person who converts "pending approval" into "cleared to open," this role is for you.
What You Will Be Doing
Obtain full legal and operational authorization to launch schools across jurisdictions more quickly and thoroughly than conventional permitting timelines permit.
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 They’re tearing down the outdated one-size-fits-all model and replacing it with AI-driven personalized learning that helps kids master academics in just two hours a day.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-AnnArbor-HeadofComplian
2 Hour Learning is scaling the fastest school model in the United States. Every new site depends on securing the right licenses, permits, and operational approvals—accurately and on schedule. You will determine what's needed, coordinate filings across jurisdictions, and ensure timely approvals. You'll leverage AI and automation tools, but you'll also engage directly with officials, follow up with contractors, and resolve edge cases that require human judgment.
This position is designed for someone who operates effectively under pressure and tight deadlines. You'll be part of a fast-moving organization with substantial resources and support, where both speed and precision are expected. You'll apply AI-enabled tools to streamline bureaucratic processes, reduce permitting cycles, and deliver outcomes rather than process documents.
If you're ready to be the person who converts "pending approval" into "cleared to open," this role is for you.
What You Will Be Doing
- Coordinating with architects, contractors, and legal counsel to obtain all necessary construction and educational-operation permits.
- Managing municipal permitting and inspection workflows across multiple jurisdictions — reducing timelines and removing obstacles.
- Compiling and submitting complete approval packages: permits, applications, compliance filings, and inspection records.
- Tracking project progress and compliance exposure in real time — ensuring full visibility and no unexpected setbacks.
- Traveling to project sites approximately 75% of the time to engage directly with local authorities, inspectors, and service providers.
- Waiting for others to flag problems or finish submissions — you will own the complete delivery process.
- Operating primarily from an office — this is a field-based execution role, not administrative support.
- Applying a uniform, one-size-fits-all approach — you'll develop custom solutions where standard processes don't exist.
- Treating delays as unavoidable — both speed and accuracy define success in this position.
- Depending on outdated tools or spreadsheets — you'll be expected to build automation and refine workflows continuously.
Obtain full legal and operational authorization to launch schools across jurisdictions more quickly and thoroughly than conventional permitting timelines permit.
Basic Requirements
- Located in the United States and authorized to work without requiring visa sponsorship.
- Willing and able to travel approximately 75% of the time to locations across U.S. states and cities.
- 5 years leading permitting, construction, or facility expansion initiatives that involved physical infrastructure and regulatory clearance.
- 5 years coordinating multiple contractors per project across different jurisdictions.
- Documented history of delivering projects ahead of schedule while maintaining full regulatory compliance.
- Experience delivering progress updates to both technical teams and executive leadership.
- Proven ownership mindset — you served as the sole accountable contact for project execution and issue resolution.
- AI-native approach — you proactively use automation and rapid iteration to accelerate delivery.
- Written communication that is precise, actionable, and relied upon by senior leadership.
- Strong regulatory judgment — you understand when to escalate, seek clarification, or challenge requirements.
- Experience in construction management, educational facility operations, or multi-location retail rollouts.
- Background developing or refining AI-driven tools for permitting, compliance, or regulatory processes.
- Direct experience working with fire marshals, building inspectors, and education licensing authorities.
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-AnnArbor-HeadofComplian
Salary : $200,000