Head of Compliance 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
Description
Elite operators don't wait for permission. They create it.
As Head of Compliance Operations, you'll transform regulatory barriers into launch pathways. Every new campus we open begins with your work—securing the complex web of approvals that makes expansion possible across all 50 states. You're not drafting policies; you're delivering the operational backbone that powers our growth.
You'll leverage cutting-edge AI tools to generate jurisdiction-specific memos and automate filings at unprecedented speed, while applying the critical human judgment that technology can't replace. When others see regulatory ambiguity, you see decision points. While committees debate approach, you ship results. The intelligent systems you build will become the single source of truth that legal, operations, and executive teams rely on daily.
This is a frontline builder role for someone who thrives on speed, ownership, and real-world regulatory judgment. You won't just maintain compliance—you'll architect it.
What you will be doing
- Deliver decisive legal research memos within 48 hours that translate complex regulatory frameworks into actionable go/no-go recommendations using AI-accelerated tools
- Assemble and submit comprehensive state-specific filing bundles with zero dependency gaps—including exemption letters, licensing forms, and legal entity documentation
- Maintain real-time approval tracking through custom-configured dashboards, with proactive escalation protocols that identify blockers before deadlines approach
- Resolve edge-case rejections and cross-state regulatory conflicts, owning the entire compliance lifecycle from submission to final approval
- Continuously optimize our AI and automation infrastructure by testing outputs, refining workflows, and implementing updates that drive measurable improvements in accuracy and speed
What you will NOT be doing
- Waiting for solutions from legal or product teams—you're the authority who finds answers or builds systems that deliver them
- Following outdated compliance playbooks—your approach is dynamic, AI-enhanced, and continuously evolving
- Conducting rework on incomplete filings—your deliverables are thorough, accurate, and finalized well before deadlines
- Communicating status through fragmented email chains—you maintain transparent, audit-ready tracking systems accessible to all stakeholders
- Treating compliance as a theoretical exercise—you own concrete outcomes that directly impact launch timelines and organizational growth
Key responsibilities
Design, implement, and execute the tech-enabled compliance systems that secure and maintain all legal approvals necessary for 2 Hour Learning to launch and operate schools at scale across the United States.
Candidate requirements
- U.S.-based and authorized to work without sponsorship
- Prepared to travel 50-75% of time across U.S. jurisdictions
- Minimum 5 years of experience in compliance, permitting, legal operations, or multi-state regulatory environments
- Proven record of delivering results in fast-paced, ambiguous regulatory landscapes
- Advanced proficiency with AI tools (ChatGPT, Claude, Perplexity) and low-code platforms (Retool, Airtable, Klair, Zapier)
- Exceptional execution speed—consistently delivers filings and research within 48-hour windows, closes loops independently
- Superior communication precision—creates decision-ready memos, concise summaries, and audit-compliant tracking systems
Nice to have
- Experience with AI prompt engineering, regulatory database management, or workflow design in compliance-intensive environments
- Demonstrated ability to identify and resolve complex regulatory edge cases before they become operational blockers
Applying for a role? Here’s what to expect.
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