Head of AI Operations, 2 Hour Learning (Remote) - $200,000/year USD

Operations isn't a support function—it's our competitive advantage.

At 2 Hour Learning, We're Building a Revolutionary Network Of AI-native K-12 Schools Where Operational Excellence Directly Drives Our Expansion Velocity. Our Operations Team Stands At The Forefront Of Our Ambitious Growth, With Each Team Member Becoming a Specialized Domain Expert Through Hands-on Implementation And AI-enhanced Skill Development Across Five Critical Areas

• Authorization & Permitting – Navigate complex regulatory landscapes to secure multi-state approvals and expedite local permitting processes, unlocking new markets with precision.
• Physical Build-Out & Maintenance – Transform empty spaces into vibrant learning environments through meticulous oversight of construction, upgrades, and vendor relationships.
• Operational Setup – Ensure flawless school launches with perfectly configured systems—from devices to platforms to compliance frameworks.
• Financial Operations – Architect budgetary frameworks, develop real-time financial intelligence dashboards, and maintain impeccable financial controls across our expanding network.
• PMO – Drive critical tech and marketing initiatives through sophisticated vendor management, dynamic progress tracking, and strategic reporting.
  
  

Your impact will be immediate and tangible: crafting financial dashboards that illuminate previously hidden insights, designing error-reducing onboarding systems, breaking into new regulatory territories, launching campuses at unprecedented speed, or creating AI workflows that revolutionize traditional management approaches. This is execution at its highest level—for builders who thrive on solving complex challenges.

If you instinctively build solutions rather than schedule discussions when facing obstacles, you'll excel here. Your systems will power our ambitious expansion of 25-30 new schools in the coming year, setting the gold standard for hundreds of staff members and thousands of students. Your results will tell the story of your success.

What You Will Be Doing

• Taking full ownership of a critical operations domain: Authorization, Build-Out, Setup, Finance, or PMO
• Pioneering innovative solutions within your domain through AI integration, automation strategies, and continuous improvement cycles
• Developing comprehensive specifications, interactive dashboards, and scalable operational playbooks that function seamlessly across our expanding school network
• Navigating and optimizing real-world operational constraints including vendor relationships, regulatory requirements, technical systems, and staff capabilities
• Engaging in strategic campus visits to implement solutions and validate their effectiveness in real educational environments
  
  

What You Won’t Be Doing

• Passively waiting for technical teams to build operational tools—you'll create prototypes and automation solutions independently
• Taking shortcuts with AI by generating generic documentation—you'll develop nuanced, field-tested solutions that deliver measurable results
• Working exclusively from headquarters—expect regular travel and on-the-ground implementation responsibilities
• Creating strategies for others to execute—you'll own the full solution lifecycle from conception through implementation
  
  

Head Of AI Operations Key Responsibilities

Own and drive exceptional outcomes within your specialized operations pillar by architecting, implementing, and refining systems that enable rapid school expansion while maintaining unwavering standards of quality, efficiency, and AI-enhanced precision.

Basic Requirements

• North American residency with capability to travel 10-40% as operational needs dictate
• Minimum 5 years of experience in high-velocity, self-directed operational roles
• Demonstrated proficiency leveraging AI tools for research, content creation, complex problem-solving, and workflow automation
• Exceptional analytical capabilities and written communication skills
• Action-oriented mindset combined with low ego and high accountability
• Specialized experience in at least one core domain: permitting processes, construction management, educational technology systems, financial planning & analysis, or vendor relationship management
• Working knowledge of productivity and operational platforms such as Klair, Syft, Wrike, Retool, or comparable low-code development environments
• Proven ability to rapidly master new domains (legal frameworks, financial systems, compliance requirements, technical platforms, 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.

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 $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-Washingt-HeadofAIOperat