Senior Director School Operations, 2 Hour Learning - $200,000/year USD - #309385

You visit a campus and immediately spot what's wrong — the ceiling tile no one reported, the HVAC system that's been making noise for days, the landscaping contractor who completed only half the checklist yet submitted a full invoice. You don't wait for feedback from a parent. You fix it before anyone realizes there was a problem.

That awareness defines this role. 2 Hour Learning runs premium K–12 facilities where families invest in an environment that is secure, reliable, and visitor-ready every day — not only during scheduled events. You will maintain that expectation throughout the Northeast: Manhattan serves as your home base, with frequent trips to campuses in CT, MA, and PA. Your efforts determine whether a school feels premium or quietly deteriorates between leadership check-ins.

Year one focuses heavily on establishing standards and vendor accountability — defining what "ready" means, building the inspection schedule, removing underperforming vendors, and training Campus Coordinators and Site Specialists to follow a consistent operating routine. As the region expands and your systems mature, the position evolves into steady-state regional oversight: you become the operator the organization turns to when a new site launches, a crisis arises, or a standard requires revision.

This is a field position. If you prefer to lead from behind a screen, this role is not suitable. If you want direct responsibility for ensuring 25+ schools maintain a premium standard daily — and the authority to deliver that outcome — continue reading.

What You Will Be Doing

• Performing scheduled on-site inspections across Northeast locations using documented standards for cleanliness, HVAC, safety, security, signage, landscaping, furniture, and visitor-readiness — and converting findings into confirmed corrective actions
• Responding to facilities issues and emergencies, coordinating vendor response, and closing work orders only after solutions are verified complete (urgent within 24 hours, routine within 1 week)
• Overseeing local vendor delivery against service-level agreements, removing vendors who fail consistently, renegotiating contracts, and conducting direct accountability discussions on quality and budget
• Establishing a weekly operational cadence with Campus Coordinators and Site Specialists to ensure each location follows standard procedures, not improvisation
• Overseeing significant campus improvement projects (HVAC replacement, interior updates, landscaping, AV/network infrastructure) on time and within budget, with minimal impact on students
• Documenting enterprise standards and AI-enabled procurement workflows (leveraging ticketing platforms, IoT/predictive maintenance systems, and centralized sourcing) to ensure uniform campus launch and operations
• Delivering concise weekly written updates on regional quality, vendor performance, escalations, and capital expenditure variance
  
  

What You Won’t Be Doing

• Leading from behind a computer — this position demands consistent physical presence at Manhattan and 20–40% travel to regional campuses (CT, MA, PA)
• Planning new campuses from the ground up or managing construction projects — capital expansion is handled by a separate team
• Developing company-wide procurement strategy independently of field operations — your standards emerge from direct site observation
• Receiving clear reporting structures and direct authority over every individual whose performance you depend on — you will create accountability through precision, written documentation, and refusing to accept unclear vendor commitments
• Treating "visitor-ready only during leadership visits" as acceptable — repeated problems are investigated for root causes, not simply re-logged
• Operating in reactive firefighting mode by default — the inspection rhythm and predictive maintenance tools are designed to identify failures before they generate complaints
  
  

Senior Director School Operations Key Responsibilities

Maintain every campus in the Northeast region in a safe, premium, and visitor-ready state every day.

Basic Requirements

• Located in New York City or within commuting range, prepared to work primarily from the Manhattan campus with 20–40% regional travel
• Authorized to work in the United States without requiring visa sponsorship
• 5+ years managing multi-site facilities, regional operations, hospitality operations, retail operations, or school operations
• Demonstrated ability to hold vendor-managed services accountable for quality, cost, and SLA performance across multiple sites
• Hands-on experience addressing urgent facilities problems (safety, HVAC, security, cleanliness) with measurable customer-experience outcomes
• Consistent written operational discipline: issue tracking, escalation documentation, vendor follow-up, weekly regional quality summaries
• Proven use of contemporary operations platforms (ticketing systems, IoT/predictive maintenance, AI-assisted procurement or planning)
  
  

Nice-to-have Requirements

• Multi-site operations leadership in premium hospitality, luxury retail, private K–12, or healthcare networks serving demanding clientele
• Experience building or rehabilitating a regional operations framework where the previous approach depended on individual heroics instead of documented standards
• History of removing underperforming vendors and developing a reliable local vendor network
• Experience directing capital improvement projects (HVAC, AV/network infrastructure, landscaping, interior updates) in active, customer-facing settings
• Familiarity with an AI-first operational model where playbooks, dashboards, and predictive tools handle routine tasks so people concentrate on decision-making
  
  

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-5714-US-Elizabet-SeniorDirector.002