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
If you've ever led construction, permitting, or facility openings and thought, "There's a smarter way to do this," this role is designed for you.
2 Hour Learning is launching schools faster than any model in the nation. But speed requires precision—every license, permit, and regulatory filing must be executed correctly and submitted on schedule. Your job is to determine requirements, sequence filings strategically, and ensure approvals arrive when needed. You'll leverage AI-powered tools and automation systems while also engaging directly with contractors, local authorities, and inspectors to resolve challenges automation alone can't solve.
This position suits someone who operates effectively under pressure and complexity. You'll be embedded in a fast-moving organization with substantial backing and infrastructure, where delivering at pace is standard and quality is mandatory. You'll deploy AI to accelerate bureaucratic processes, reduce permitting delays, and produce results—not just documentation.
If you're ready to be the operator who converts "pending approval" into "cleared for launch," this is the opportunity.
What you will be doing
- Orchestrating architects, contractors, and legal counsel to obtain all necessary construction and operational permits for education facilities.
- Managing municipal permitting and inspection workflows across multiple jurisdictions — reducing timelines and removing obstacles.
- Assembling and filing complete approval packages: permit applications, regulatory submissions, and inspection records.
- Overseeing project progress and compliance exposure across the portfolio — ensuring full transparency and no unexpected delays.
- Traveling to project sites (~75%) to engage in person with local regulators, inspectors, and service providers to maintain momentum.
What you will NOT be doing
- Waiting for escalation or relying on others to finalize submissions — you'll own delivery from start to finish.
- Operating remotely from a desk full-time — this role requires on-the-ground execution, not administrative support.
- Following a standardized, jurisdiction-agnostic process — you'll design custom solutions as requirements shift.
- Treating delays as unavoidable — precision and velocity define this position.
- Using outdated systems or spreadsheet-based tracking — automation and continuous improvement are expected.
Key responsibilities
Obtain complete legal and operational authorization to operate educational facilities across jurisdictions with greater speed and thoroughness than conventional permitting workflows deliver.
Candidate requirements
- Located in the United States and eligible to work without requiring visa sponsorship.
- Available and willing to travel approximately 75% of the time to U.S. cities and states.
- 5+ years leading permitting, construction, or facilities expansion initiatives involving physical infrastructure and regulatory compliance.
- 5+ years coordinating multiple contractors per project across varying jurisdictions.
- Documented history of delivering projects ahead of deadline while maintaining full regulatory compliance.
- Experience communicating project status to technical teams and executive leadership.
- Clear ownership record — you served as the sole accountable party for project outcomes and issue resolution.
- AI-fluent mindset — you default to automation and rapid iteration to accelerate execution.
- Written communication that is precise, actionable, and dependable for senior stakeholders.
- Strong regulatory intuition — you understand when to escalate, seek clarity, or challenge requirements.
Nice to have
- Experience in construction management, education facilities, or multi-location retail rollouts.
- Track record designing or refining AI solutions for permitting, compliance, or regulatory operations.
- Direct interaction history with fire marshals, building inspectors, and education licensing authorities.
Applying for a role? Here’s what to expect.
Crossover's skill assessment process combines innovative AI power with decades of human research, to take the guesswork, human bias, and pointless filters out of recruiting high-performing teams.
Chat-style
screening interview.
Cognitive 
aptitude test.
Prove real-world 
job skills.
Interview with the hiring manager.
Accept job offer.
Pass
proctored test.
Frequently asked questions
Reviews
Meet some people who've landed similar jobs
Recruitment sucks. So we’re fixing it.
The Olympics of work
It’s super hard to qualify—extreme quality standards ensure every single team member is at the top of their game.
Premium pay for premium talent
Over 50% of new hires double or triple their previous pay. Why? Because that’s what the best person in the world is worth.
Shortlist by skills, not bias
We don’t care where you went to school, what color your hair is, or whether we can pronounce your name. Just prove you’ve got the skills.
Join the world's largest community of 
AI-first remote workers.