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Crossover

Head of Compliance & Permitting, 2 Hour Learning (Remote) - $200,000/year USD

Crossover, Piedmont, South Dakota, United States, 57769

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Head of Compliance & Permitting, 2 Hour Learning (Remote) - $200,000/year USD 2 days ago Be among the first 25 applicants

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This range is provided by Crossover. Your actual pay will be based on your skills and experience — talk with your recruiter to learn more.

Base pay range $100.00/hr - $100.00/hr

If you've managed construction permitting for schools, hospitals, or commercial sites and thought, "This process could move faster without sacrificing accuracy," this role is for you. 2 Hour Learning is scaling the fastest school model in the nation. Every new campus depends on timely regulatory approval. Licenses, permits, and compliance filings must be executed correctly and without delay. You will determine requirements, sequence submissions appropriately, and ensure approvals arrive on schedule. You will leverage AI tools and automation systems, but you will also engage directly with officials, coordinate contractors, and resolve edge cases that automation cannot address. This position suits someone who excels under complexity and tight timelines. You will operate within a high-velocity organization that provides unlimited resources and support, where speed is standard and quality is mandatory. You will apply AI tools to streamline bureaucratic processes, reduce permitting cycles, and deliver results, not just documentation. If you are prepared to transform "pending approval" into "cleared to open," this is the opportunity.

What You Will Be Doing

Aligning 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.

Assembling and filing complete approval packages: permits, applications, regulatory submissions, inspection records.

Tracking project progress and compliance exposure across all initiatives — ensuring real-time transparency and no unexpected delays.

Traveling to project sites (~75%) to engage directly with local authorities, inspectors, and service providers to sustain momentum.

What You Won’t Be Doing

Relying on others to flag problems or finalize submissions — you will control the full delivery process.

Executing tasks remotely from a central office — this is a field-driven role, not an administrative one.

Applying a rigid, location‑specific playbook — you will develop custom solutions for novel challenges.

Treating delays as unavoidable — speed and accuracy define this position.

Using outdated tools or manual status tracking — you will be expected to automate workflows and refine them continuously.

Head Of Compliance & Permitting Key Responsibilities Obtain complete legal and operational authorization to launch schools across jurisdictions with greater speed and thoroughness than conventional permitting pathways deliver.

Basic Requirements

Located in the U.S. and legally authorized to work without requiring visa sponsorship.

Prepared to travel approximately 75% of the time to U.S. cities and states.

5+ years directing permitting, construction, or facility expansion initiatives that involved physical infrastructure and regulatory clearance.

5+ years coordinating multiple contractors per project across different jurisdictions.

Documented success delivering projects ahead of target dates while maintaining full regulatory compliance.

Experience delivering progress briefings to both technical teams and executive leadership.

Clear evidence of ownership — you served as the sole accountable party for project outcomes and issue resolution.

AI-native approach — you default to automation and rapid iteration to accelerate execution.

Written communication that is precise, actionable, and relied upon by senior leadership.

Strong regulatory judgment — you understand when to elevate, seek clarification, or challenge requirements.

Nice-to-have Requirements

Experience in construction management, education operations, or multi-location retail rollout.

Background developing or refining AI-driven tools for permitting, compliance, or regulatory processes.

Prior collaboration with fire marshals, building inspectors, and education regulatory bodies.

About 2 Hour Learning 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 matters. 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.

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-COUNTRY-HeadofComplian2.002

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