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Senior Director School Operations, Learning; Remote

Remote / Online - Candidates ideally in
Chicago, Cook County, Illinois, 60290, USA
Listing for: Crossover
Full Time, Part Time, Remote/Work from Home position
Listed on 2026-01-04
Job specializations:
  • Management
    Healthcare Management
  • Education / Teaching
Salary/Wage Range or Industry Benchmark: 200000 USD Yearly USD 200000.00 YEAR
Job Description & How to Apply Below
Position: Senior Director School Operations, 2 Hour Learning (Remote) - $200,000/year USD

Senior Director School Operations

Join Crossover as the Senior Director of School Operations for 2 Hour Learning. This remote position offers a salary of $100 per hour (equivalent to $200,000 per year) and is a full‑time role focusing on ensuring operational consistency across all campuses.

Responsibilities
  • Lead the Campus Coordinator function nationally, managing hiring, onboarding, coaching, performance management, and terminations.
  • Own all campus‑level operational policies, covering safety, compliance, family experience, and front‑of‑house delivery.
  • Collaborate with Campus Coordinators and Lead CCs to identify policy gaps, recurring challenges, and operational inconsistencies, and address them with systemic solutions.
  • Create comprehensive playbooks, SOPs, and training resources that translate organizational expectations into everyday actions at each site.
  • Define performance benchmarks, review frequencies, and escalation protocols to ensure rapid and uniform problem resolution.
  • Conduct regular operational audits across campuses to confirm policy comprehension, implementation, and positive outcomes for families and staff.
What You Won’t Be Doing
  • Oversee the daily operations of a single campus.
  • Focus primarily on facilities improvements or construction initiatives.
  • Create policies that remain theoretical documents without influencing actual behavior.
  • Act as a detached HR liaison rather than a hands‑on people leader.
  • Tolerate a season‑to‑season campus culture that justifies inconsistent operations.
Key Responsibilities

Guarantee that every campus delivers consistent, high‑caliber operational execution by directing the Campus Coordinator function, owning operational policy development, and maintaining accountability to defined standards across all teams.

Basic Requirements
  • 7+ years in operations leadership, people management, or multi‑site contexts requiring consistency and execution.
  • Documented experience recruiting, coaching, and performance‑managing frontline operational leaders across multiple locations.
  • Sound judgment regarding safety, compliance, customer experience, and risk oversight.
  • Proven capability to detect policy deficiencies and convert uncertainty into actionable, practical standards.
  • Confident in providing candid feedback and making difficult decisions when performance is inadequate.
  • Willingness to travel up to 50% to U.S. campuses.
  • U.S.

    -based and authorized to work without requiring sponsorship.
Nice-to-Have Requirements
  • Experience in education, hospitality, healthcare, or similar high‑trust, customer‑facing sectors.
  • Track record of developing centralized training programs, playbooks, or operational standards for geographically dispersed teams.
  • Experience leading managers, transitioning from individual contributor or player‑coach to leader‑of‑leaders.
About 2 Hour Learning

2 Hour Learning is redefining education with AI‑driven personalized learning that helps children master academics in just two hours a day. They boast student rankings in the top 1–2% nationally and a 6.5x growth rate for the top 20% of learners. Their mission is to make learning smarter, faster, and more accessible through AI.

Working With Us

This is a full‑time (40 hours per week), long‑term position. The role is immediately available and requires entering into an independent contractor agreement with Crossover as a Contractor of Record. Compensation is $100 USD per hour, paid weekly. For detailed payment information, consult Crossover FAQ.

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Position Requirements
10+ Years work experience
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