Director of Operations & Automation, 2 Hour Learning (Remote) - $200,000/year USD

Elite Operators Wanted: Build the Infrastructure for Education's Future

At 2 Hour Learning, operations isn't just a support function—it's our product. Our national network of AI-native K-12 schools scales only when our systems excel. That's why we need operators who don't just maintain—they build, automate, and transform. You'll master one of five critical domains through immersive experience and AI-accelerated learning, creating the infrastructure that powers educational innovation at scale.

This is high-stakes, high-velocity execution. You'll ship financial dashboards that eliminate blind spots. Design onboarding systems that slash student setup errors. Secure multi-state regulatory approvals. Launch campuses in record time. Create AI workflows that replace traditional management layers. We need builders, not bystanders—operators who see bottlenecks and start coding solutions, not scheduling meetings.

Your systems will power our next 30 schools. Your work will define excellence for hundreds of staff and thousands of students. Your impact will be immediate, measurable, and transformative.

What You Will Be Doing

• Own one critical operations pillar: Authorization, Build-Out, Setup, Finance, or PMO
• Pioneer solutions to novel challenges using AI, automation, and rapid iteration
• Create scalable specifications, dashboards, and runbooks that standardize excellence across dozens of schools
• Navigate complex real-world constraints across vendors, regulators, systems, and staff
• Deploy on-site when necessary to implement or validate your solutions in the field

What You Won’t Be Doing

• Waiting for technical teams to build your tools—you'll prototype and automate independently
• Settling for superficial AI-generated documentation—you'll develop functional solutions that deliver results
• Operating exclusively from headquarters—expect regular travel and on-site implementation
• Delegating execution after strategy development—you'll drive complete ownership from concept to delivery

Director Of Operations & Automation Key Responsibilities

Own and deliver exceptional outcomes within your assigned operations pillar by building systems that enable rapid school expansion with uncompromising speed, accuracy, and AI-native precision.

Basic Requirements

• North America-based with capacity for 25-75% travel as operations demand
• 5+ years of proven experience in high-velocity, autonomous operations roles
• Exceptional analytical capabilities and written communication skills
• Demonstrated bias for action, minimal ego, and maximum ownership
• Specialized experience in at least one core domain: regulatory compliance, facilities management, SaaS implementation, financial planning, or vendor management
• Advanced AI utilization skills—employing AI tools with the fluency others use spreadsheets
• Proven track record building automations, systematizing workflows, and implementing practical AI solutions
• Demonstrated ability to rapidly master new domains (legal, finance, compliance, systems)

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 for more details on this topic.

Crossover Job Code: LJ-5461-US-SandySpr-DirectorofOper1.004