Crossover
Director of Operations & Automation, 2 Hour Learning (Remote) - $200,000/year US
Crossover, Florida, New York, United States
Director of Operations & Automation, 2 Hour Learning (Remote) - $200,000/year USD
Base pay range
$100.00/hr - $100.00/hr
Operations Overview Operations isn't a support function here—it's the foundation of everything we do.
At 2 Hour Learning, Our AI-native K-12 School Network Runs On The Strength Of Our Campus Operations. The Operations Team Doesn't Assist Expansion—they Make It Possible. Every Team Member Specializes In One Of Five Essential Operational Domains, Mastering It Rapidly Through Hands-on Experience And AI‑enhanced Learning.
Authorization & Permitting – Navigate multi-state legal frameworks and expedite local permits to open new markets.
Physical Build‑Out & Maintenance – Manage campus construction, facility improvements, and contractor oversight to deliver and maintain exceptional learning environments.
IT Operational Setup – Deploy comprehensive technology ecosystems—hardware, software, support infrastructure, compliance tools—for every new school launch.
Financial Operations – Develop budgets, create real-time reporting dashboards, and ensure audit‑compliant financial governance across all campuses and business units.
PMO – Drive execution of strategic technology and marketing projects through vendor performance tracking, executive dashboards, and project-level analytics.
You'll create dashboards that expose critical financial insights. Engineer onboarding processes that cut student setup failures in half. Win regulatory clearance in untapped states. Launch campuses at unprecedented speed. Or design AI-driven workflows that eliminate traditional management overhead. This is mission-critical, high-tempo execution—built by doers, not observers.
If you're an operator who identifies friction points and immediately starts building solutions—not convening committees—this role will suit you. Your infrastructure will enable the 25–30 schools we're opening over the next year. Your execution will set the standard for hundreds of team members and thousands of learners. And your results will demonstrate your capability.
What You Will Be Doing
Taking ownership of one strategic operations pillar: Authorization, Build‑Out, Platforms, Finance, or PMO.
Addressing novel challenges in your domain through AI tools, workflow automation, and iterative testing.
Creating detailed specifications, performance dashboards, or operational guides that function across multiple campuses.
Engaging directly with operational realities: facility contractors, regulatory bodies, technology platforms, and campus personnel.
Visiting school sites as required to deploy or validate your operational solutions.
What You Won't Be Doing
Depending on product or engineering teams to create your operational tools—you'll build prototypes and automation yourself.
Using AI to generate generic SOPs without real functionality—you'll vibe‑code practical solutions that deliver results.
Operating exclusively from headquarters—travel and on‑site implementation are expected.
Delegating execution of your strategic plans—you'll own both strategy and delivery from start to finish.
Director Of Operations & Automation Key Responsibilities Deliver measurable results in your designated operations pillar by designing and implementing systems that enable rapid school expansion with precision, reliability, and AI‑native methodology.
Basic Requirements
Located in North America with flexibility to travel 25-75% based on operational needs.
5+ years in high-velocity, high-autonomy operational roles.
Excellent analytical capabilities and written communication.
Action-oriented mindset, collaborative approach, full accountability.
Background in at least one of: regulatory compliance, facilities development, SaaS implementation, FP&A, or technology vendor oversight.
Leverages AI as naturally as others use spreadsheets: routinely, intuitively, and for diverse applications.
History of creating automation, systematizing processes, and exploring vibe‑coding for practical gains or personal interest.
Demonstrated ability to quickly gain expertise in complex domains (legal, financial, compliance, technical systems, etc.).
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.
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 $100 USD/hour, which equates to $200,000 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-5461-US-CoralSpr-DirectorofOper1.008
Seniority level
Director
Employment type
Full-time
Job function
Information Technology, Engineering, and Product Management
Industries
Software Development, Education Administration Programs, and IT Services and IT Consulting
#J-18808-Ljbffr
Operations Overview Operations isn't a support function here—it's the foundation of everything we do.
At 2 Hour Learning, Our AI-native K-12 School Network Runs On The Strength Of Our Campus Operations. The Operations Team Doesn't Assist Expansion—they Make It Possible. Every Team Member Specializes In One Of Five Essential Operational Domains, Mastering It Rapidly Through Hands-on Experience And AI‑enhanced Learning.
Authorization & Permitting – Navigate multi-state legal frameworks and expedite local permits to open new markets.
Physical Build‑Out & Maintenance – Manage campus construction, facility improvements, and contractor oversight to deliver and maintain exceptional learning environments.
IT Operational Setup – Deploy comprehensive technology ecosystems—hardware, software, support infrastructure, compliance tools—for every new school launch.
Financial Operations – Develop budgets, create real-time reporting dashboards, and ensure audit‑compliant financial governance across all campuses and business units.
PMO – Drive execution of strategic technology and marketing projects through vendor performance tracking, executive dashboards, and project-level analytics.
You'll create dashboards that expose critical financial insights. Engineer onboarding processes that cut student setup failures in half. Win regulatory clearance in untapped states. Launch campuses at unprecedented speed. Or design AI-driven workflows that eliminate traditional management overhead. This is mission-critical, high-tempo execution—built by doers, not observers.
If you're an operator who identifies friction points and immediately starts building solutions—not convening committees—this role will suit you. Your infrastructure will enable the 25–30 schools we're opening over the next year. Your execution will set the standard for hundreds of team members and thousands of learners. And your results will demonstrate your capability.
What You Will Be Doing
Taking ownership of one strategic operations pillar: Authorization, Build‑Out, Platforms, Finance, or PMO.
Addressing novel challenges in your domain through AI tools, workflow automation, and iterative testing.
Creating detailed specifications, performance dashboards, or operational guides that function across multiple campuses.
Engaging directly with operational realities: facility contractors, regulatory bodies, technology platforms, and campus personnel.
Visiting school sites as required to deploy or validate your operational solutions.
What You Won't Be Doing
Depending on product or engineering teams to create your operational tools—you'll build prototypes and automation yourself.
Using AI to generate generic SOPs without real functionality—you'll vibe‑code practical solutions that deliver results.
Operating exclusively from headquarters—travel and on‑site implementation are expected.
Delegating execution of your strategic plans—you'll own both strategy and delivery from start to finish.
Director Of Operations & Automation Key Responsibilities Deliver measurable results in your designated operations pillar by designing and implementing systems that enable rapid school expansion with precision, reliability, and AI‑native methodology.
Basic Requirements
Located in North America with flexibility to travel 25-75% based on operational needs.
5+ years in high-velocity, high-autonomy operational roles.
Excellent analytical capabilities and written communication.
Action-oriented mindset, collaborative approach, full accountability.
Background in at least one of: regulatory compliance, facilities development, SaaS implementation, FP&A, or technology vendor oversight.
Leverages AI as naturally as others use spreadsheets: routinely, intuitively, and for diverse applications.
History of creating automation, systematizing processes, and exploring vibe‑coding for practical gains or personal interest.
Demonstrated ability to quickly gain expertise in complex domains (legal, financial, compliance, technical systems, etc.).
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.
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 $100 USD/hour, which equates to $200,000 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-5461-US-CoralSpr-DirectorofOper1.008
Seniority level
Director
Employment type
Full-time
Job function
Information Technology, Engineering, and Product Management
Industries
Software Development, Education Administration Programs, and IT Services and IT Consulting
#J-18808-Ljbffr