Head of Compliance & Permitting
$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
Semi-flexible schedule
Fully-remote
full-time (40 hrs/week)
Long-term role

Head of Compliance & Permitting   $200,000 USD/year

Description

If you've managed construction permitting for schools, hospitals, or commercial sites and thought, "This process could move faster without sacrificing accuracy," this role is for you.

2 Hour Learning is scaling the fastest school model in the nation. Every new campus depends on timely regulatory approval. Licenses, permits, and compliance filings must be executed correctly and without delay. You will determine requirements, sequence submissions appropriately, and ensure approvals arrive on schedule. You will leverage AI tools and automation systems, but you will also engage directly with officials, coordinate contractors, and resolve edge cases that automation cannot address.

This position suits someone who excels under complexity and tight timelines. You will operate within a high-velocity organization that provides unlimited resources and support, where speed is standard and quality is mandatory. You will apply AI tools to streamline bureaucratic processes, reduce permitting cycles, and deliver results, not just documentation.

If you are prepared to transform "pending approval" into "cleared to open," this is the opportunity.

What you will be doing

  • Aligning architects, contractors, and legal counsel to obtain all necessary construction and educational operation permits.
  • Managing municipal permitting and inspection workflows across multiple jurisdictions — reducing timelines and removing obstacles.
  • Assembling and filing complete approval packages: permits, applications, regulatory submissions, inspection records.
  • Tracking project progress and compliance exposure across all initiatives — ensuring real-time transparency and no unexpected delays.
  • Traveling to project sites (~75%) to engage directly with local authorities, inspectors, and service providers to sustain momentum.

What you will NOT be doing

  • Relying on others to flag problems or finalize submissions — you will control the full delivery process.
  • Executing tasks remotely from a central office — this is a field-driven role, not an administrative one.
  • Applying a rigid, location-specific playbook — you will develop custom solutions for novel challenges.
  • Treating delays as unavoidable — speed and accuracy define this position.
  • Using outdated tools or manual status tracking — you will be expected to automate workflows and refine them continuously.

Key responsibilities

Obtain complete legal and operational authorization to launch schools across jurisdictions with greater speed and thoroughness than conventional permitting pathways deliver.

Candidate requirements

  • Located in the U.S. and legally authorized to work without requiring visa sponsorship.
  • Prepared to travel approximately 75% of the time to U.S. cities and states.
  • 5+ years directing permitting, construction, or facility expansion initiatives that involved physical infrastructure and regulatory clearance.
  • 5+ years coordinating multiple contractors per project across different jurisdictions.
  • Documented success delivering projects ahead of target dates while maintaining full regulatory compliance.
  • Experience delivering progress briefings to both technical teams and executive leadership.
  • Clear evidence of ownership — you served as the sole accountable party for project outcomes and issue resolution.
  • AI-native approach — you default to automation and rapid iteration to accelerate execution.
  • Written communication that is precise, actionable, and relied upon by senior leadership.
  • Strong regulatory judgment — you understand when to escalate, seek clarification, or challenge requirements.

Nice to have

  • Experience in construction management, education operations, or multi-location retail rollout.
  • Background developing or refining AI-driven tools for permitting, compliance, or regulatory processes.
  • Prior collaboration with fire marshals, building inspectors, and education regulatory bodies.

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

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.
STEP 1

Chat-style
screening interview.

Cognitive 
aptitude test.
STEP 2

Cognitive 
aptitude test.

Prove real-world 
job skills.
STEP 3

Prove real-world 
job skills.

Interview with the hiring manager.
STEP 4

Interview with the hiring manager.

Accept job offer.
STEP 6

Accept job offer.

Pass
proctored test.
STEP 5

Pass
proctored test.

Frequently asked questions

About Crossover

Meet some people who've landed similar jobs

Why Crossover

Recruitment sucks. So we’re fixing it.

The Olympics of work

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

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

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.

Crossover Logo White
Follow us on
Have a question?

Get answers to common questions using our smart chatbot Crosby.

HELP AND FAQs

Join the world's largest community of AI first Remote WorkersAI-first remote workers.