Head of Compliance & Permitting

@ Trilogy

Overview

Become the regulatory pathfinder who transforms legal obstacles into launch opportunities. As the Head of Compliance & Permitting, you will chart the course that allows new educational campuses to open across America by mastering the regulatory landscape of all 50 states.

Role Description

This position is not about enforcing rules, but about creating possibilities. Using cutting-edge AI tools alongside your regulatory instincts, you will revolutionize compliance practices, identify ambiguities, evaluate risk levels, and drive decision-making to overcome challenges.

What You Will Be Doing

• Produce comprehensive legal research memos within 48 hours using AI-enhanced tools.
• Craft and submit flawless state-specific compliance packages.
• Develop and maintain real-time approval tracking systems with platforms like Airtable, Klair, or Retool.
• Resolve complex regulatory challenges from submission through final approval.
• Enhance AI and automation infrastructure through workflow improvements.

What You Won’t Be Doing

• Waiting for direction from legal or product teams.
• Following outdated compliance protocols without innovation.
• Conducting after-the-fact corrections or cleanup.
• Communicating progress through fragmented email chains.
• Treating compliance as a theoretical exercise.

Key Responsibilities

Design, implement, and manage technology-enhanced compliance systems that secure and maintain legal authorizations for 2 Hour Learning to launch and operate educational facilities across the United States at scale.

Basic Requirements

• U.S.-based candidate with work authorization without sponsorship.
• Ability to travel extensively (50-75% of time) across multiple U.S. jurisdictions.
• Minimum 5 years of experience in compliance management or related fields.
• Advanced proficiency with AI tools and low-code platforms (Retool, Airtable, Klair, Zapier).
• Exceptional execution speed and superior communication skills.

Nice-to-have Requirements

• Experience with AI prompt engineering and specialized regulatory databases.
• History of identifying and resolving complex regulatory edge cases.

About 2 Hour Learning

2 Hour Learning is reprogramming education for the AI era by replacing outdated models with AI-driven personalized learning. They value talent, performance, and innovative solutions to fix a broken school system.

Working with Us

This is a full-time, long-term position available immediately as an independent contractor through Crossover. The role pays $100 USD/hour, equivalent to $200,000 USD/year, with weekly payment.

Key skills/competency

• Compliance
• Permitting
• Regulatory
• AI tools
• Legal research
• Risk assessment
• Low-code platforms
• Communication
• Tracking systems
• Problem solving