Are you ready to redefine operational excellence through AI? At 2 Hour Learning, we’re transforming K-12 education with our groundbreaking model that delivers 2.6x academic growth in just two-hour learning blocks. Our mission is clear: leverage AI to scale this revolutionary approach while maintaining exceptional student outcomes. This is not just about efficiency—it’s about pioneering a new standard in education.

We’re looking for an operational genius who can take complex processes and automate them with AI-first solutions. Not just someone who’s used AI, but a true technical leader who can implement it—connecting systems, running API calls, and creating intelligent frameworks that drive strategic insights.

You’ll work directly with the founder, driving strategic decision-making and having significant ownership and oversight of operational frameworks that power our growth. This role demands a relentless pursuit of excellence and the ability to thrive in a high-expectation, fast-paced environment.

If you’re ready to lead the operational AI revolution and have the strategic vision to scale an innovative educational model, this is your opportunity to make a profound impact.

What You Will Be Doing

• Building AI-Powered Systems: Designing and implementing AI-driven operational frameworks that optimize efficiency and maintain exceptional educational outcomes at scale.
• Strategic Decision Support: Leveraging AI tools to deliver real-time strategic insights to the founder, identifying growth opportunities, and mitigating risks before they arise.
• Cross-Functional Leadership: Managing large-scale, cross-functional operational portfolios to ensure seamless integration of AI solutions across all aspects of the business.
• Hands-on AI Implementation: Utilizing technical skills to connect systems, run API calls, and automate complex processes—no delegating the technical work.
• Driving Operational Excellence: Implementing AI-enabled quality control systems to maintain consistent delivery of our academic model across multiple locations.

What You Won’t Be Doing

• Day-to-Day Campus Operations: Your focus is on strategic scaling and automation, not managing individual campus operations.
• Curriculum Development or Educational Staff Oversight: This role is about operational excellence, not educational content or teaching.
• High-Level Theorizing Without Implementation: We need real, technical usage of AI—not just strategic ideas or conceptual applications.
• Maintaining Status Quo: There’s no room for complacency—this is a high-growth, high-intensity role that demands constant innovation.

Head Of Facilities Management Key Responsibilities

Design and implement AI-powered operational frameworks and automated systems that enable scalable growth and consistent delivery of 2 Hour Learning’s academic model while providing actionable, data-driven strategic insights to the founder.

Basic Requirements

• 10+ years of operational leadership experience scaling multi-location businesses (education or high-end retail, hospitality, or healthcare).
• Prior experience at a top-tier management consulting firm (e.g., McKinsey, Bain, BCG)
• Proficient in practical and technical usage of AI tools; must pass a rigorous assessment that involves automating business processes using AI.
• Experience converting operational processes into AI-driven systems with demonstrable technical implementation (coding, API integrations, automation).
• History of managing large-scale, cross-functional operational portfolios, driving strategic transformation, and achieving high-level business outcomes.
• Proven track record of developing and presenting strategic recommendations to C-suite executives, specifically the ability to translate complex operational data into clear, actionable executive-level insights
• Based in the United States and willing to travel 30% of the time to campus locations.
• Must be legally eligible to work in the US without visa sponsorship.

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-4410-US-Chicago-HeadofFaciliti.005