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

You walk into a building and immediately spot what's wrong — the ceiling tile that wasn't reported, the HVAC system that's been making noise for days, the landscaping contractor who billed for work they didn't complete. You don't wait for complaints. You fix problems before they become visible.

That mindset defines this position. 2 Hour Learning runs high-quality K–12 campuses where families expect an environment that is secure, reliable, and ready for visitors every single day — not only during scheduled events. You will maintain that expectation across the Northeast region: Manhattan serves as your home base, with recurring visits to facilities in CT, MA, and PA. Your work determines whether a campus maintains a premium standard or quietly deteriorates between leadership reviews.

Year one focuses heavily on establishing standards and vendor accountability — defining what "ready" means, implementing audit protocols, replacing underperforming contractors, and establishing repeatable operating routines for Campus Coordinators and Site Specialists. As the region expands and your systems mature, the role transitions toward ongoing regional oversight: you become the operational authority the organization depends on during new campus launches, urgent situations, or standard revisions.

This is a hands-on field position. If you prefer dashboard-based management, this role is not suitable. If you want direct responsibility for maintaining premium standards across 25 schools — and the authority to deliver results — continue reading.

What You Will Be Doing

Performing scheduled on-site inspections across Northeast facilities against established standards for cleanliness, HVAC systems, safety protocols, security, signage, landscaping, furniture condition, and visitor readiness — and ensuring findings result in confirmed corrective actions

Responding to facilities problems and emergencies, coordinating contractor response, and closing work orders only after verification of completed repairs (urgent issues <24 hours, standard requests <1 week)

Overseeing local contractor performance against service level agreements, terminating consistently underperforming vendors, renegotiating contract terms, and conducting direct accountability discussions regarding quality and pricing

Establishing a weekly operational cadence with Campus Coordinators and Site Specialists to ensure consistent campus operations based on standard procedures rather than individual effort

Overseeing significant campus improvement projects (HVAC system updates, interior design updates, landscaping work, AV/networking infrastructure) delivered on time and within budget with minimal student impact

Developing organization-wide standards and AI-powered procurement frameworks (leveraging ticketing platforms, IoT/predictive maintenance systems, and centralized purchasing) to ensure uniform campus launch and operation

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

What You Won’t Be Doing

• Operating remotely from a dashboard — this position demands regular on-site presence at Manhattan and 20–40% travel time to regional locations (CT, MA, PA)
• Leading new campus design or managing ground-up construction projects — capital expansion falls under a separate team
• Developing enterprise procurement strategy removed from operational reality — your standards emerge from direct site observation
• Working within established reporting structures with direct authority over all personnel affecting your outcomes — you'll create accountability through documentation, written follow-through, and rejection of ambiguous contractor commitments
• Treating "visitor-ready only during leadership visits" as acceptable — persistent problems require root cause analysis, not repeated work orders
• Operating in constant reactive firefighting mode — the inspection schedule and predictive maintenance systems enable you to identify issues before they generate complaints
  
  

Senior Director School Operations Key Responsibilities

Maintain every Northeast region campus at safe, premium, and tour-ready standards 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 requirements
• Authorized to work legally in the United States without requiring visa sponsorship
• 5 years managing multi-site facilities, regional operations, hospitality operations, retail operations, or school operations
• Documented success maintaining vendor-managed service accountability for quality standards, cost control, and SLA compliance across multiple sites
• Hands-on experience addressing urgent facilities problems (safety concerns, HVAC failures, security issues, cleanliness standards) with quantifiable customer experience outcomes
• Established written operational discipline: issue tracking, escalation documentation, vendor correspondence, weekly regional quality reporting
• Confirmed experience with contemporary operations platforms (ticketing systems, IoT/predictive maintenance tools, AI-supported procurement or planning systems)
  
  

Nice-to-have Requirements

• Multi-site operations leadership experience in premium hospitality, luxury retail, private K–12 education, or healthcare organizations serving demanding clientele
• Experience building or rehabilitating regional operating frameworks where previous approaches depended on individual heroics instead of standardized procedures
• Proven history of terminating underperforming contractors and developing replacement vendor networks
• Experience directing capital improvement initiatives (HVAC systems, AV/networking infrastructure, landscaping projects, interior renovations) in active, customer-facing facilities
• Background operating in AI-first environments where automated playbooks, dashboards, and predictive tools handle routine tasks so personnel 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-Philadel-SeniorDirector.001