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

You conduct a walkthrough and immediately identify what's wrong — the ceiling tile that was never reported, the HVAC return making noise for days, the landscaping contractor who completed half the scope and billed for everything. You don't wait for someone to raise a concern. You resolve it before it becomes visible.

That awareness defines this position. 2 Hour Learning runs premium K–12 facilities where families invest in an experience that is secure, reliable, and visitor-ready every single day — not only when events are scheduled. You will be accountable for maintaining that benchmark throughout the Northeast: Manhattan serving as your anchor location, with frequent site visits to schools across CT, MA, and PA. Your execution determines whether a campus maintains a premium standard or quietly deteriorates between leadership reviews.

Year one emphasizes establishing protocols and vendor accountability — defining what "operational readiness" means, implementing the inspection schedule, removing underperforming service providers, and training Campus Coordinators and Site Specialists on sustainable operating procedures. As additional schools join the region and your systems mature, the role transitions to ongoing regional oversight: you become the operational expert the organization depends on during new campus launches, urgent situations, or protocol revisions.

This is a site-based position. If you prefer managing through reports and metrics alone, this role will not suit you. If you want direct responsibility for ensuring 25 schools maintain premium standards daily — and the autonomy to deliver that outcome — continue reading.

What You Will Be Doing

• Executing scheduled site inspections throughout Northeast locations against written standards covering cleanliness, HVAC, safety, security, signage, landscaping, furniture, and visitor-readiness — then ensuring findings result in confirmed corrective action
• Managing facilities incidents and urgent issues, coordinating service providers, and closing work orders only once resolution is confirmed on-site (urgent within 24 hours, standard within 1 week)
• Overseeing vendor execution against service-level agreements, removing consistently underperforming contractors, renegotiating contract terms, and conducting direct accountability discussions regarding quality and budget
• Establishing a consistent weekly operational rhythm with Campus Coordinators and Site Specialists to ensure every location follows standardized procedures rather than ad hoc responses
• Overseeing significant facility improvements (HVAC system updates, interior design refreshes, landscaping projects, AV/networking installations) delivered on time and within budget with minimal impact on students
• Developing enterprise-wide operational standards and AI-supported procurement processes (leveraging work order platforms, IoT/predictive maintenance systems, and centralized vendor sourcing) to ensure uniform campus launch and operation
• Delivering concise weekly written updates on regional facility quality, vendor execution, escalated issues, and capital expenditure tracking
  
  

What You Won’t Be Doing

• Operating remotely from reports alone — this position demands consistent on-site presence at Manhattan and 20–40% travel throughout the region (CT, MA, PA)
• Leading new campus design or managing ground-up construction projects — capital expansion responsibilities belong to a separate function
• Developing company-wide procurement policies without field validation — your standards emerge from direct site observation
• Working within established org charts with direct authority over all personnel affecting your outcomes — you will create accountability through documentation, written follow-through, and refusal to accept ambiguous vendor commitments
• Tolerating "visitor-ready only during leadership tours" as acceptable — repeating problems get investigated for root cause, not simply re-reported
• Defaulting to reactive crisis management — the inspection schedule and predictive maintenance tools exist to identify failures before they generate complaints
  
  

Senior Director School Operations Key Responsibilities

Maintain every campus across the Northeast region as safe, premium, and visitor-ready on a daily basis.

Basic Requirements

• Located in New York City or within commuting range, prepared to work primarily from the Manhattan campus with 20–40% travel to regional sites
• Authorized to work in the United States without requiring visa sponsorship
• 5 years managing multi-site facilities, regional operations, hospitality management, retail operations, or educational facility operations
• Documented success holding vendor-managed service providers accountable for quality standards, cost control, and SLA compliance across distributed locations
• Hands-on experience addressing urgent facility problems (safety, HVAC, security, cleanliness) with measurable impact on customer experience
• Established written communication discipline: incident tracking, escalation documentation, vendor correspondence, weekly regional performance summaries
• Confirmed experience with contemporary operations platforms (work order systems, IoT/predictive maintenance, AI-enabled procurement or planning tools)
  
  

Nice-to-have Requirements

• Regional operations leadership in premium hospitality, high-end retail, private K–12 education, or healthcare systems serving demanding clientele
• Experience building or restructuring a regional operations framework where the previous approach depended on individual heroics instead of documented standards
• History of terminating underperforming service providers and developing a reliable local contractor network
• Background delivering capital improvement initiatives (HVAC, AV/networking, landscaping, interior renovations) within active, customer-facing facilities
• Familiarity with AI-driven operational environments where automated systems, dashboards, and predictive tools handle routine tasks so personnel concentrate on strategic decisions
  
  

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-Connecti-SeniorDirector.001