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

Regulatory Pathfinder Wanted: The Person Who Makes "Impossible" Launches PossibleThis isn't about policy theory. It's about regulatory execution. You'll be the force that transforms legal barriers into launch runways, securing the complex web of approvals that enable our schools to open across all 50 states. From entity formations to license acquisitions to navigating exemption mazes, you own the mission-critical work that transforms regulatory challenges into operational reality.You'll leverage cutting-edge AI tools to generate jurisdiction-specific analyses and accelerate filings, while applying the critical human judgment that spots ambiguities, flags risks, and drives decisions. While others debate hypotheticals, you deliver tangible outcomes. Your intelligent systems and dashboards will become the definitive source of truth for legal, operations, and executive leadership.This is a frontline builder role that demands velocity, ownership, and sophisticated regulatory judgment. You won't just maintain compliance—you'll architect it.What You Will Be DoingDeliver AI-powered legal research memos that transform complex regulatory landscapes into actionable recommendations within 48-hour turnaroundsConstruct and submit comprehensive state-specific filing packages—including exemption documentation, licensing applications, and entity formation materials—with zero dependency gapsMaintain real-time approval tracking through self-configured dashboard systems (Airtable, Klair, Retool), with proactive escalation protocols for blockers and automated deadline alertsResolve complex regulatory rejections, reconcile multi-state compliance conflicts, and drive approvals from submission to final authorizationContinuously enhance our AI and automation infrastructure by validating outputs, engineering workflows, and implementing updates that drive precision and efficiencyWhat You Won’t Be DoingDepending on legal or product teams for solutions—you identify answers independently or build systems that deliver themOperating from static compliance protocols—your environment is dynamic, AI-enhanced, and continuously evolvingManaging remediation work or correcting deficient filings—your deliverables are thorough, accurate, and completed ahead of deadlinesCommunicating status through fragmented email chains—all stakeholders access a centralized, audit-ready tracking systemTreating compliance as theoretical—you drive concrete outcomes that directly impact launch timelines and market presenceHead Of Compliance & Permitting Key ResponsibilitiesSecure and maintain the comprehensive legal authorizations enabling 2 Hour Learning to launch and operate educational institutions nationwide—through the design, ownership, and execution of scalable, technology-driven compliance systems.Basic RequirementsU.S.-based with authorization to work without sponsorshipPrepared for 50-75% travel across U.S. jurisdictionsMinimum 5 years of experience in compliance management, regulatory permitting, legal operations, or multi-state business expansionProven history of delivering results in fast-paced, ambiguous regulatory environmentsAdvanced proficiency with AI platforms (ChatGPT, Claude, Perplexity) and low-code development tools (Retool, Airtable, Klair, Zapier)Execution-focused professional—consistently delivers research and filings within 48-hour windows and completes tasks without follow-upExceptional communicator—produces decision-enabling memos, concise summaries, and documentation that withstands regulatory scrutinyNice-to-have RequirementsExperience with AI prompt engineering, regulatory database management, or workflow design in compliance-intensive sectorsDemonstrated ability to identify and resolve complex regulatory obstacles before they impact operationsAbout 2 Hour LearningEducation 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 usThis 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-SandySpr-HeadofComplian