Trilogy
Senior Director of Regulatory Operations, 2 Hour Learning (Remote) - $400,000/ye
Trilogy, Indianapolis, Indiana, us, 46262
Senior Director of Regulatory Operations, 2 Hour Learning (Remote) - $400,000/year USD Join to apply for the
Senior Director of Regulatory Operations, 2 Hour Learning (Remote) - $400,000/year USD
role at
Trilogy Senior Director of Regulatory Operations, 2 Hour Learning (Remote) - $400,000/year USD 1 day ago Be among the first 25 applicants 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 Permission and Progress
Submit your CV and any additional required information after you have read this description by clicking on the application button.
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
Managing regulatory timelines across 25–30 campus launches Leading state-level authorization, licensing, and school compliance filings Running local permitting processes (zoning, fire, building, operational, etc.) Coordinating with legal, real estate, and launch ops to align execution Developing and owning a repeatable playbook to reduce time-to-launch Building trusted relationships with city, state, and agency officials across jurisdictions
What You Won’t Be Doing
Following a playbook — you'll be expected to build one Monitoring from the sidelines — this role is about securing approvals, not tracking status Choosing between pace and precision — here, both are non-negotiable Managing one location at a time — you'll run parallel launches across multiple states Working in isolation — this role sits at the center of legal, facilities, and launch ops Hiding in process — your job is to simplify, accelerate, and unblock Delegating responsibility for regulatory risk — you own the timeline
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 looking for a senior operator who's navigated regulatory complexity at scale — whether from a top-tier consulting firm (MBB preferred, not required) or a high-stakes role in education, healthcare, real estate, or another compliance-heavy industry.
You Should Bring
3+ years leading complex, multi-stakeholder projects with high regulatory, legal, or operational complexity (e.g., market entry, M&A, infrastructure rollout) Experience owning timelines and deliverables across functions (e.g., legal, ops, external stakeholders) with a track record of removing bottlenecks and delivering outcomes Proven ability to navigate opaque or fragmented regulatory environments, even without subject-matter expertise — and build trust with government, legal, or compliance bodies Exceptional structured problem solving, communication, and stakeholder management skills, developed in a high-performance consulting environment Comfort operating with urgency, autonomy, and accountability in a fast-scaling or startup-like context Comfort using AI tools to accelerate workflows, even if you're not technical U.S. work authorization and availability to travel domestically ~25% (about 1 week/month)
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-Indianap-SeniorDirector.003
Seniority level
Seniority levelExecutive Employment type
Employment typeFull-time Job function
Job functionLegal, Engineering, and Project Management IndustriesEducation Administration Programs, Hospitality, and Business Consulting and Services Referrals increase your chances of interviewing at Trilogy by 2x Sign in to set job alerts for “Senior Director of Operations” roles. Indiana, United States $43.00-$48.70 2 weeks ago Indianapolis, IN $65,000.00-$80,000.00 1 week ago We’re unlocking community knowledge in a new way. Experts add insights directly into each article, started with the help of AI.
#J-18808-Ljbffr Remote working/work at home options are available for this role.
Senior Director of Regulatory Operations, 2 Hour Learning (Remote) - $400,000/year USD
role at
Trilogy Senior Director of Regulatory Operations, 2 Hour Learning (Remote) - $400,000/year USD 1 day ago Be among the first 25 applicants 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 Permission and Progress
Submit your CV and any additional required information after you have read this description by clicking on the application button.
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
Managing regulatory timelines across 25–30 campus launches Leading state-level authorization, licensing, and school compliance filings Running local permitting processes (zoning, fire, building, operational, etc.) Coordinating with legal, real estate, and launch ops to align execution Developing and owning a repeatable playbook to reduce time-to-launch Building trusted relationships with city, state, and agency officials across jurisdictions
What You Won’t Be Doing
Following a playbook — you'll be expected to build one Monitoring from the sidelines — this role is about securing approvals, not tracking status Choosing between pace and precision — here, both are non-negotiable Managing one location at a time — you'll run parallel launches across multiple states Working in isolation — this role sits at the center of legal, facilities, and launch ops Hiding in process — your job is to simplify, accelerate, and unblock Delegating responsibility for regulatory risk — you own the timeline
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 looking for a senior operator who's navigated regulatory complexity at scale — whether from a top-tier consulting firm (MBB preferred, not required) or a high-stakes role in education, healthcare, real estate, or another compliance-heavy industry.
You Should Bring
3+ years leading complex, multi-stakeholder projects with high regulatory, legal, or operational complexity (e.g., market entry, M&A, infrastructure rollout) Experience owning timelines and deliverables across functions (e.g., legal, ops, external stakeholders) with a track record of removing bottlenecks and delivering outcomes Proven ability to navigate opaque or fragmented regulatory environments, even without subject-matter expertise — and build trust with government, legal, or compliance bodies Exceptional structured problem solving, communication, and stakeholder management skills, developed in a high-performance consulting environment Comfort operating with urgency, autonomy, and accountability in a fast-scaling or startup-like context Comfort using AI tools to accelerate workflows, even if you're not technical U.S. work authorization and availability to travel domestically ~25% (about 1 week/month)
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-Indianap-SeniorDirector.003
Seniority level
Seniority levelExecutive Employment type
Employment typeFull-time Job function
Job functionLegal, Engineering, and Project Management IndustriesEducation Administration Programs, Hospitality, and Business Consulting and Services Referrals increase your chances of interviewing at Trilogy by 2x Sign in to set job alerts for “Senior Director of Operations” roles. Indiana, United States $43.00-$48.70 2 weeks ago Indianapolis, IN $65,000.00-$80,000.00 1 week ago We’re unlocking community knowledge in a new way. Experts add insights directly into each article, started with the help of AI.
#J-18808-Ljbffr Remote working/work at home options are available for this role.