Job Details

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

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

This role is remote and based in the U.S. It involves designing and operating tech-enabled compliance systems to launch and operate schools across the U.S.

Overview

This is a frontline builder role focused on compliance operations. You will secure regulatory greenlights, manage entity filings, license approvals, and state exemptions. You will work with AI tools to generate memos and automate filings while acting as the human in the loop to identify ambiguity, escalate blockers, and drive decisions. You will ship results, test intelligent workflows, and maintain live dashboards used by legal, ops, and executive teams.

What You Will Be Doing

• Deliver AI-accelerated legal research memos translating regulatory frameworks into go/no-go recommendations within 48 hours.
• Build and submit state-specific filing bundles, including exemption letters, licensing forms, and legal entity documentation, acknowledging dependencies.
• Track every approval in real time using configurable dashboards (e.g., Airtable, Klair, Retool); escalate blockers and trigger alerts before deadlines.
• Troubleshoot edge-case rejections, resolve cross-state conflicts, and own the final mile from submission to signed-off approval.
• Continuously refine the AI and automation stack by testing outputs and designing workflows to improve accuracy and speed.

What You Wont Be Doing

• Waiting on legal or product to hand you answers you will find them or build the system to obtain them.
• Working with static checklists or outdated compliance playbooks this role is dynamic and AI-driven.
• Running backend rework or fixing sloppy filings your work should be clean, complete, and signed off before deadlines.
• Reporting status via email threads you will use live, audit-ready trackers accessible to stakeholders.
• Managing compliance like an academic exercise you own outcomes that impact launch dates and public visibility.

Key Responsibilities

Secure and maintain legal approvals to launch and operate schools across the U.S. by designing, owning, and executing scalable, tech-enabled compliance systems.

Basic Requirements

• Based in the U.S. and authorized to work without sponsorship
• Willing to travel 5075% of the time across U.S. jurisdictions
• 5+ years in compliance, permitting, legal operations, or multi-state operations
• Demonstrated track record of owning outcomes in fast-moving, ambiguous environments
• Daily user of AI tools (e.g., ChatGPT, Claude, Perplexity) and low-code platforms (e.g., Retool, Airtable, Klair, Zapier)
• High-speed executor delivers filings or research within 48 hours and closes loops without prompting
• Precise communicator writes decision-ready memos, crisp summaries, and audit-proof trackers

Nice-to-have Requirements

• Familiarity with AI prompt engineering, regulatory databases, or designing workflows in compliance-heavy environments
• Track record of proactively spotting and solving edge-case regulatory blockers

About 2 Hour Learning

Education is being reimagined with AI-driven personalized learning. 2 Hour Learning aims to help students master academics in just two hours a day, with strong national performance indicators and a dynamic work environment for innovators, educators, and AI specialists.

Working with us

This is a full-time (40 hours per week), long-term position. The role is immediately available and requires entering into an independent contractor agreement with Crossover as a Contractor of Record. Compensation is $100 USD/hour (~$200,000/year) with weekly payment. For details, see www.crossover.com/help-and-faqs.

Job Details

• Seniority level: Director
• Employment type: Full-time
• Job function: Legal, Engineering, and Strategy/Planning
• Industries: Education Administration Programs, Legal Services, and Business Consulting and Services

Note: This description is for the Head of Compliance Operations role at 2 Hour Learning. Other job postings listed in the source are not part of this description.