Licensing & Permitting Director $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
Hybrid location
full-time (40 hrs/week)
Flexible schedule
Long-term role
Description
You don't need a law degree... but you do need to be the person Legal calls when they're stuck.
This role isn't about policy. It's about permission. You'll be the one who makes it possible for new schools to open, securing the regulatory greenlights that power every campus launch. From entity filings to license approvals to edge-case exemptions, you will own the work that unlocks legal operation across all 50 states.
You'll use AI tools like a RAG Bot to generate jurisdiction-specific memos and automate filings in record time, but you're also the human in the loop who spots ambiguity, flags red/yellow risks, escalates blockers, and gets decisions made. While others debate strategy, you ship results. You'll test and refine intelligent workflows, push updates to live dashboards, and make sure nothing slips through the cracks. The systems you build will be the source of truth for legal, ops, and executive teams.
This isn't a support role. It's a frontline builder job — one that requires speed, ownership, and real-world regulatory judgment. You won't just keep the trains running. You'll lay the track.
What you will be doing
- Deliver AI-accelerated legal research memos that translate fragmented 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 — without missing a dependency.
- Track every approval in real time using dashboards you configure (e.g., Airtable, Klair, Retool), escalating blockers and triggering alerts before deadlines hit.
- Troubleshoot edge-case rejections, resolve cross-state conflicts, and own the final mile of compliance — from submission to signed-off approval.
- Continuously refine the AI and automation stack by testing outputs, designing workflows, and pushing updates that improve accuracy and speed.
What you will NOT be doing
- Waiting on legal or product to hand you answers — you're expected to find them or build the system that will.
- Working with static checklists or outdated compliance playbooks — this job is dynamic, AI-driven, and constantly evolving.
- Running backend rework or fixing sloppy filings — your work is clean, complete, and signed off before deadlines, not after.
- Reporting status via email threads — every stakeholder sees what you see in a live, audit-ready tracker.
- Managing compliance like an academic exercise — you own outcomes that impact launch dates and public visibility.
Key responsibilities
Secure and maintain the legal approvals that allow 2 Hour Learning to launch and operate schools across the U.S. — by designing, owning, and executing tech-enabled compliance systems that work at scale.
Candidate requirements
- Based in the U.S. and authorized to work without sponsorship
- Willing to travel 50–75% of the time across U.S. jurisdictions
- 5+ years in compliance, permitting, legal ops, or multi-state operations
- Demonstrated track record of owning outcomes in fast-moving, ambiguous domains
- 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, closes loops without prompting
- Precision communicator — writes decision-ready memos, crisp summaries, and audit-proof trackers
Nice to have
- 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
How it works
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.
STEP 1
Chat-style
screening interview.
STEP 2
Cognitive 
aptitude test.
STEP 3
Prove real-world 
job skills.
STEP 4
Interview with the hiring manager.
STEP 5
Accept Job Offer.
ONE LAST THING
Pass 
proctored test.
Frequently asked questions
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Why Crossover
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.