Senior Director of Regulatory Operations, 2 Hour Learning (Remote) - $400,000/year USD

Trilogy; Norman (OK); Remote; USD 200,000; Full time

Job summary

A leading education innovation company seeks a Senior Director of Regulatory Operations to oversee the regulatory landscape for multiple campus launches. The ideal candidate will have a strong background in navigating complex compliance environments and demonstrate leadership abilities to expedite processes. This role offers a unique opportunity to influence the education sector and drive operational success.

Qualifications

• 10+ years leading complex permitting across U.S. jurisdictions.
• Proven experience in school licensing and regulatory workflows.
• Exceptional communication and results ability under ambiguity.

Responsibilities

• Orchestrating regulatory timelines across 25-30 campus launches.
• Spearheading state-level authorization and compliance filings.
• Creating scalable playbooks to reduce time-to-launch.

Skills

Navigating complex compliance environments

Leadership in regulatory processes

Communication with legal teams

Proficiency in AI tools for optimization

Job description

Senior Director of Regulatory Operations, 2 Hour Learning (Remote) - $400,000/year USD

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Senior Director of Regulatory Operations, 2 Hour Learning (Remote) - $400,000/year USD

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Join to apply for the Senior Director of Regulatory Operations, 2 Hour Learning (Remote) - $400,000/year USD role at Trilogy

This range is provided by Trilogy. Your actual pay will be based on your skills and experience — talk with your recruiter to learn more.

Base pay range

$200.00/hr - $200.00/hr

Master Regulatory Strategist: The Difference Between Permits and Progress

If you've managed complex regulatory approvals across states, cities, fire codes, school boards, or health departments, you already know the difference between following a checklist and clearing the path for launch.

2 Hour Learning is launching 25–30 new campuses in the next six months. These aren't theoretical plans. We have the funding, we've proven the model, and we're executing at pace. To make it happen, we need someone to own the greenlight; a systems thinker who doesn't just interpret regulations, but drives timelines across them.

You'll lead all state-level authorizations and local permitting. This includes zoning, fire safety, building code, operational registration, and everything in between. You won't be tracking status from the sidelines — you'll be accountable for the timing, relationships, and bottleneck removal that gets campuses open.

About 2 Hour Learning

2 Hour Learning powers Alpha Schools, NextGen Academy, GT School, Texas Sports Academy, and Unbound Academy — a growing family of K–12 schools and education products built around one proven idea: students can achieve a full year of academic growth in just two focused hours per day. The rest of the day is theirs — for sailing, sports, public speaking, or game design.

Our platform combines real-time progress dashboards, curriculum recommendations, and feedback tools — giving students and guides the structure they need to go fast, and the space they need to grow.

We're private equity-backed, with long-term funding and a mandate to scale. This isn't a test. The model works. Charter applications are live. Campuses are expanding. Now we're building the infrastructure to bring it everywhere it can work.

WHY THIS ROLE?

This is an exceptional opportunity for post-consulting operators looking for real authority, real ownership, and real-world impact — without needing to become a founder.

You'll Have

• Decision rights, not just influence
• A model that already works — and the resources to scale it
• Direct impact on the education system, with none of the nonprofit drag
• Startup urgency with financial backing and a growing national footprint
  
  

You'll also be working directly with a founding team that's obsessed with speed, data, and real-world outcomes — not buzzwords or slow-moving boards. This group has launched companies, scaled platforms, and already proven the model. Now they want a builder who can cut through red tape and get schools open.

ARE YOU THE RIGHT FIT?

If you've ever looked at a launch timeline and thought, "I could make this run faster and cleaner, if they'd just let me own it" — this is the role where you get to prove it.

What You Will Be Doing

• Orchestrating regulatory timelines across 25–30 simultaneous campus launches, ensuring no delays
• Spearheading all state-level authorization, licensing, and compliance filings with precision and foresight
• Executing local permitting processes (zoning, fire, building, operational) with strategic efficiency
• Aligning execution across legal, real estate, and operations teams to eliminate bottlenecks
• Creating and implementing a scalable regulatory playbook that systematically reduces time-to-launch
• Establishing authoritative relationships with city, state, and agency officials across multiple jurisdictions
  
  

What You Won’t Be Doing

• Following a predetermined playbook — your mandate is to build the definitive system
• Simply reporting status updates — your role demands securing approvals, not tracking them
• Sacrificing quality for speed or vice versa — excellence in both is the standard
• Managing sequential launches — you'll be orchestrating multiple parallel approvals across states
• Operating in a silo — you'll serve as the critical nexus between legal, facilities, and operations
• Creating bureaucratic processes — your mission is to simplify, accelerate, and eliminate obstacles
• Diffusing regulatory accountability — you own the timeline and its outcomes
  
  

Senior Director Of Regulatory Operations Key Responsibilities

Deliver complete, on-time regulatory clearance across all campuses — enabling each site to open on schedule, legally and operationally.

Basic Requirements

We're seeking an exceptional regulatory strategist who has navigated complex compliance environments at scale — whether from a top-tier consulting background (MBB preferred, not required) or through high-impact leadership in education, healthcare, real estate, or another highly regulated industry.

You Must Demonstrate

• 10+ years leading complex permitting or approval processes across multiple U.S. jurisdictions
• Proven experience with school licensing, capital projects, or multi-agency regulatory workflows
• Exceptional record of delivering results under ambiguity — rapidly, thoroughly, and independently
• Sophisticated communication skills across legal teams, vendors, and government agencies
• Proficiency leveraging AI tools to optimize workflows, even without technical expertise
• U.S. work authorization and capacity for 25% domestic travel (approximately one week monthly)
  
  

About 2 Hour Learning

Education is broken, but 2 Hour Learning is proving it doesn’t have to be. They’re tearing down the outdated one-size-fits-all model and replacing it with AI-driven personalized learning that helps kids master academics in just two hours a day.

With students consistently ranking in the top 1-2% nationally and the top 20% achieving an astonishing 6.5x growth, they’re proving that smarter learning is possible. At 2 Hour Learning, it’s talent and performance that matter.

They offer a dynamic, on-campus and remote-friendly environment where innovators, educators, and AI specialists can be a part of fixing a broken school system.

2 Hour Learning is reprogramming learning for the AI era.

Here’s How They’re Fixing It.

There is so much to cover for this exciting role, and space here is limited. Hit the Apply button if you found this interesting and want to learn more. We look forward to meeting you!

Working with us

This is a full-time (40 hours per week), long-term position. The position is immediately available and requires entering into an independent contractor agreement with Crossover as a Contractor of Record. The compensation level for this role is $200 USD/hour, which equates to $400,000 USD/year assuming 40 hours per week and 50 weeks per year. The payment period is weekly. Consult www.crossover.com/help-and-faqs for more details on this topic.

Crossover Job Code: LJ-5624-US-Norman-SeniorDirector

Seniority level

• Seniority level

  Executive

Employment type

• Employment type

  Full-time

Job function

• Job function

  Legal, Engineering, and Project Management

• Industries

  Education Administration Programs, Hospitality, and Business Consulting and Services

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