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

You enter a facility and immediately spot what's wrong — the unfiled report about a damaged ceiling tile, the HVAC system that's been making noise for days, the landscaping contractor who completed only part of the agreed scope yet submitted a full invoice. You don't wait for a complaint to surface. You resolve issues before they become visible problems.

That ability defines this position. 2 Hour Learning runs high-caliber K–12 facilities where families expect an environment that is secure, reliable, and inspection-ready at all times — not solely during scheduled events. You will establish and maintain that benchmark throughout the Northeast: Manhattan serves as your home base, supplemented by routine travel to campuses in CT, MA, and PA. Your execution determines whether a campus maintains premium quality or slowly deteriorates between leadership reviews.

Year one will emphasize establishing standards and restructuring vendor relationships — documenting operational readiness criteria, implementing audit protocols, transitioning underperforming vendors, and training Campus Coordinators and Site Specialists on sustainable operational routines. Once the region expands and your systems mature, the position transitions to regional operational leadership: you become the resource the organization relies on for new campus launches, crisis response, or standards refinement.

This is a hands-on operational role. If you prefer remote oversight via reporting tools, this position will not suit you. If you want direct responsibility for ensuring 25+ campuses deliver premium quality daily — and the autonomy to achieve that outcome — continue reading.

What You Will Be Doing

Executing scheduled on-site inspections across Northeast locations using documented benchmarks for cleanliness, HVAC performance, safety protocols, security measures, signage, landscaping, furniture condition, and inspection readiness — then ensuring findings result in confirmed remediation

Addressing facilities problems and urgent situations, coordinating service providers, and closing work orders only after on-site confirmation of resolution (critical issues <24 hours, standard requests <1 week)

Overseeing regional vendor compliance with service-level agreements, terminating consistently underperforming contractors, renegotiating contracts, and conducting direct accountability discussions regarding quality and pricing

Establishing a consistent weekly operational cadence with Campus Coordinators and Site Specialists to ensure standardized execution rather than ad-hoc problem-solving

Managing significant campus improvement projects (HVAC replacements, interior upgrades, landscaping enhancements, AV/network installations) within timeline and budget parameters while minimizing student impact

Developing organization-wide operational standards and AI-supported procurement protocols (leveraging ticketing platforms, IoT/predictive maintenance tools, and centralized vendor sourcing) to ensure uniform campus launch and operation

Delivering concise weekly written updates covering regional quality metrics, vendor performance data, escalated issues, and capital expenditure tracking

What You Won’t Be Doing

• Operating remotely through dashboards — this position demands consistent physical presence at Manhattan and 20–40% travel to regional campuses (CT, MA, PA)
• Leading new campus design initiatives or managing ground-up construction projects — capital expansion is handled by a separate team
• Developing company-wide procurement strategy disconnected from field operations — your standards emerge from direct site observation
• Working within clean organizational hierarchies with formal authority over all personnel affecting your outcomes — you will establish accountability through documentation, written follow-through, and rejection of ambiguous vendor commitments
• Tolerating "inspection-ready only during leadership visits" as acceptable — persistent problems receive root cause analysis, not repeated work orders
• Operating in constant reactive crisis mode — your audit protocols and predictive maintenance systems are designed to identify failures before they generate complaints
  
  

Senior Director School Operations Key Responsibilities

Ensure every Northeast region campus maintains safety standards, premium quality, and inspection readiness daily.

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-location facilities, regional operations, hospitality operations, retail operations, or educational facility operations
• Documented success managing vendor-provided services for quality, cost control, and SLA compliance across multiple sites
• Hands-on experience addressing critical facilities issues (safety, HVAC, security, cleanliness) with quantifiable customer experience outcomes
• Established written operational discipline: incident tracking, escalation documentation, vendor communications, weekly regional performance summaries
• Confirmed experience with contemporary operations platforms (ticketing systems, IoT/predictive maintenance tools, AI-assisted procurement or planning)
  
  

Nice-to-have Requirements

• Regional operations leadership in premium hospitality, high-end retail, private K–12 education, or healthcare organizations serving demanding clientele
• Experience building or transforming a regional operations framework that previously depended on individual heroics rather than documented standards
• History of vendor transition and rebuilding regional vendor networks
• Experience directing capital improvement projects (HVAC, AV/network infrastructure, landscaping, interior renovations) in active, customer-facing facilities
• Background in AI-enabled operational environments where automated playbooks, dashboards, and predictive tools handle routine tasks so staff can focus 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-Philadel-SeniorDirector.002