Job Details

Director of Regulatory Operations, 2 Hour Learning (Remote) - $200,000/year USD

This role is a frontline operational executive that blends regulatory expertise with AI?driven technology. You will secure the critical approvals that enable 2?Hour Learning to launch schools across all 50 states, translating complex legal frameworks into executable pathways and building the definitive source of truth for legal, operations, and executive teams.

Base pay range

$100.00/hr - $100.00/hr

• Deliver comprehensive legal research memos within 48?hours that transform fragmented regulatory requirements into actionable recommendations, leveraging AI acceleration for speed and accuracy.
• Construct and submit flawless state?specific filing packages, including exemption documentation, licensing applications, and entity filingswith zero dependency gaps.
• Implement and maintain real?time approval tracking dashboards that provide complete visibility, proactively escalating blockers and triggering alerts well before critical deadlines.
• Resolve complex regulatory challenges including edge?case rejections and cross?jurisdictional conflicts, owning the entire approval process from submission to final authorization.
• Continuously enhance AI and automation capabilities through rigorous testing, workflow optimization, and system updates that drive measurable improvements in speed and accuracy.

• Waiting for solutions from legal or product teamsyou identify answers independently or build systems to generate them.
• Following outdated compliance protocolsyou operate in a dynamic, AI?powered environment that demands continuous innovation.
• Managing post?submission corrections or quality issuesyou deliver work that is thorough, accurate, and approved before deadlines.
• Communicating status through disorganized email chainsyou maintain transparent, audit?ready tracking systems accessible to all stakeholders.
• Treating compliance as a theoretical exerciseyou own tangible outcomes that directly impact launch timelines and organizational success.

Secure and maintain the comprehensive legal authorizations enabling 2?Hour Learning to launch and operate schools nationwide by architecting, implementing, and executing technology?enhanced compliance systems designed for scalable growth.

• U.S.-based with authorization to work without sponsorship.
• Commitment to travel 50?75% across U.S. jurisdictions.
• Minimum 5?years of proven experience in compliance, permitting, legal operations, or multi?state regulatory management.
• Demonstrated history of ownership and results in fast?paced, ambiguous regulatory environments.
• Advanced proficiency with AI tools (ChatGPT, Claude, Perplexity) and low?code platforms (Retool, Airtable, Klair, Zapier).
• Exceptional execution velocityconsistently delivers critical filings and research within 48?hour timeframes without follow?up.
• Superior communication precisioncreates decision?ready memos, concise summaries, and documentation that withstand regulatory scrutiny.

• Experience with AI prompt engineering, regulatory database navigation, or workflow design in compliance?intensive sectors.
• Proven ability to anticipate and resolve complex regulatory challenges before they become operational blockers.

Education is broken, but 2?Hour Learning is proving it doesnt have to be. Theyre 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 6.5 growth, theyre proving that smarter learning is possible. 2?Hour Learning offers a dynamic, on?campus and remote?friendly environment where innovators, educators, and AI specialists can be a part of fixing a broken school system.

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-Boston-DirectorofRegu

Seniority level

• Director

Employment type

• Full?time

Job function

• Legal, Engineering, and Project Management