Director of Regulatory Operations
$200,000 USD/year Pay is set based on global value, not the local market. Most roles = hourly rate x 40 hrs x 50 weeks 

Fully remote within the US; frequent travel
Hybrid location
full-time (40 hrs/week)
Flexible schedule
Long-term role

Director of Regulatory Operations   $200,000 USD/year

Description

Legal expertise? Not required. But when lawyers hit a wall, they'll be calling you.

This position centers on authorization, not policy creation. You'll serve as the catalyst enabling new educational institutions to launch by navigating the regulatory maze that governs campus operations. From corporate formations to licensing protocols to specialized exemptions, you'll master the compliance framework that enables legal operations nationwide.

Leveraging cutting-edge AI systems including RAG technology, you'll produce jurisdiction-tailored analyses and streamline filing processes at unprecedented speed. Yet you remain the critical human element—identifying regulatory gray areas, assessing risk levels, escalating obstacles, and driving resolution. While others theorize, you execute. You'll optimize intelligent processes, maintain live monitoring systems, and ensure zero compliance gaps. Your frameworks become the definitive resource for legal, operational, and leadership teams.

This transcends traditional support functions—it's a strategic execution role demanding velocity, accountability, and sophisticated regulatory acumen. You won't merely maintain existing operations. You'll architect the infrastructure.

What you will be doing

  • Generate AI-enhanced regulatory analysis reports that convert complex compliance landscapes into actionable launch decisions—delivered within 48-hour windows.
  • Orchestrate state-tailored submission packages encompassing exemption requests, permit applications, and corporate documentation—ensuring complete dependency mapping.
  • Monitor approval pipelines through custom-configured dashboards (Airtable, Klair, Retool), proactively flagging obstacles and activating deadline alerts.
  • Navigate complex rejection scenarios, mediate interstate regulatory conflicts, and drive compliance initiatives from initial submission through final authorization.
  • Iteratively enhance AI and automation infrastructure through output validation, workflow optimization, and system updates that boost precision and efficiency.

What you will NOT be doing

  • Depending on legal or product teams for direction—you're empowered to source solutions or architect systems that generate them.
  • Operating from rigid templates or legacy compliance frameworks—this role demands adaptability, AI integration, and continuous evolution.
  • Executing post-deadline corrections or remedial filing work—your deliverables are thorough, accurate, and completed ahead of schedule.
  • Communicating progress through email chains—all stakeholders access real-time, audit-compliant tracking systems.
  • Treating compliance as theoretical work—you drive tangible results that directly influence launch timelines and organizational visibility.

Key responsibilities

Obtain and preserve the regulatory authorizations enabling 2 Hour Learning's nationwide school deployment—through the creation, ownership, and execution of technology-powered compliance frameworks that scale effectively.

Candidate requirements

  • U.S.-based with independent work authorization (no sponsorship required)
  • Available for 50–75% travel frequency across U.S. territories
  • 5+ years experience in compliance management, regulatory affairs, legal operations, or multi-jurisdictional business development
  • Proven success driving results in rapidly-evolving, high-ambiguity environments
  • Active proficiency with AI platforms (ChatGPT, Claude, Perplexity) and automation tools (Retool, Airtable, Klair, Zapier)
  • Rapid-cycle delivery capability—completes research or filing tasks within 48-hour parameters, maintains proactive follow-through
  • Strategic communication skills—produces executive-ready analyses, concise status updates, and compliance-grade documentation

Nice to have

  • Experience with AI prompt optimization, regulatory research platforms, or compliance workflow design in heavily-regulated sectors
  • History of independently identifying and resolving non-standard regulatory challenges

Meet a successful candidate

Watch Interview
Aleks Natchkebia
Aleks  |  Strategic Analyst
Georgia  

Where do you work when your most productive time is at 3am? This night owl uses a flexible remote job to unlock career-defining performance ...

Meet Aleks

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