Senior Director of Regulatory Operations, 2 Hour Learning (Remote)

Trilogy

Chicago, IL 60604

United States

Posted July 1, 2025

{CONTRACTOR,FULL_TIME}

Nursing

Remote

Senior Level

Valid until July 31, 2025

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Job Description

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

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Trilogy provided pay range

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 for more details on this topic.
Crossover Job Code: LJ-5624-US-Chicago-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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