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

Operations here is not a support function—it is the foundation.

At 2 Hour Learning, Our AI-native K-12 School Network Depends Entirely On Flawless Campus Operations. The Operations Team Leads Expansion, Not Assists It. Every Member Specializes In One Of Five Essential Domains, Building Deep Expertise Quickly Through Hands-on Deployment And AI-enhanced Learning

• Authorization & Permitting – Obtain multi-state regulatory clearance and expedite local permitting processes to open new markets.
• Physical Build-Out & Maintenance – Manage campus construction, facility upgrades, and contractor oversight to deliver and maintain exceptional spaces.
• IT Operational Setup – Deploy every campus with complete technical infrastructure—hardware, software, support, and compliance—ready from day one.
• Financial Operations – Develop budgets, create real-time reporting dashboards, and uphold audit-grade financial discipline across all schools and business units.
• PMO – Drive execution of critical technology and marketing projects using vendor performance tracking, dashboards, and initiative-level metrics.
  
  

You will build dashboards that illuminate hidden financial risks. Create onboarding processes that cut student setup mistakes in half. Win regulatory approval in untapped states. Launch campuses faster than anyone thought possible. Or design AI-native workflows that eliminate traditional management overhead. This work demands precision and speed—from builders, not spectators.

If you are an operator who identifies friction points and immediately starts constructing solutions—not convening meetings—you will excel here. The systems you create will enable 25–30 new schools over the next year. Your contributions will set the standard for hundreds of employees and thousands of students. And your results will be undeniable.

What You Will Be Doing

• Leading one of five operational pillars: Authorization, Build-Out, Platforms, Finance, or PMO
• Addressing novel challenges in your domain through AI tools, automation, and fast experimentation
• Creating transparent specifications, dashboards, or process documentation that scales to dozens of campuses
• Engaging directly with operational realities: contractors, regulatory bodies, technology platforms, and campus teams
• Visiting school sites as necessary to deploy or validate your systems in the field
  
  

What You Won’t Be Doing

• Depending on product or engineering teams to create your operational tools—you will prototype and automate directly
• Prompting AI to "draft a procedure" and considering the job complete—you will vibe-code functional systems that deliver results
• Operating exclusively from headquarters—expect regular travel and on-campus implementation
• Delegating execution of your strategy to others—you will own both planning and delivery, start to finish
  
  

Head Of AI Operations Key Responsibilities

Take full ownership of results in your assigned pillar by designing and deploying systems that enable rapid-scale school growth with precision, speed, and AI-first methodology.

Basic Requirements

• Located in North America with flexibility to travel 25-75% as required
• 5 years in a high-velocity, high-autonomy operations environment
• Excellent analytical abilities and written communication
• Action-oriented mindset, low ego, high accountability
• Background in one of these areas: regulatory compliance, facility construction, SaaS onboarding, FP&A, or technology vendor oversight
• Applies AI as naturally as others use spreadsheets: reflexively, routinely, and across multiple contexts.
• Has designed automations, structured workflows, and explored vibe-coding for productivity or curiosity.
• Proven ability to master new domains rapidly (legal, finance, compliance, 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.

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-Denver-HeadofAIOperat.003