Director of Operations & Automation, 2 Hour Learning (Remote) - $200,000/year USD - Trilogy : Job Details

Overview

Director of Operations & Automation, 2 Hour Learning (Remote) - $200,000/year USD

Elite operators wanted: Build the machine that powers America's fastest-growing AI-native school network. At 2 Hour Learning, Operations Isn't a Support Function—it's Our Competitive Advantage. Our National Network Of AI-native K-12 Schools Expands At The Speed Of Our Systems. You'll Lead One Of Five Mission-critical Domains, Becoming An Expert Through Real-world Execution And AI-accelerated Mastery.

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.

Base pay range$100.00/hr - $100.00/hr

Responsibilities

• Lead one of five core operations pillars: Authorization, Build-Out, Setup, Finance, or PMO
• Develop AI-powered solutions for complex operational challenges within your domain
• Create scalable specifications, dashboards, and runbooks that standardize excellence across dozens of schools
• Navigate real-world constraints with regulators, vendors, systems, and staff to deliver practical solutions
• Deploy on-site when necessary to implement systems and validate their effectiveness

What You Will Be Doing

• Lead one of five core operations pillars: Authorization, Build-Out, Setup, Finance, or PMO
• Develop AI-powered solutions for complex operational challenges within your domain
• Create scalable specifications, dashboards, and runbooks that standardize excellence across dozens of schools
• Navigate real-world constraints with regulators, vendors, systems, and staff to deliver practical solutions
• Deploy on-site when necessary to implement systems and validate their effectiveness

What You Won't Be Doing

• Depending on technical teams to build your tools—you'll prototype and automate independently
• Producing theoretical documentation—your solutions must function in the real world
• Working exclusively from headquarters—expect regular field deployment and on-site execution
• Separating strategy from execution—you'll drive both from concept to completion

Director Of Operations & Automation – Key Responsibilities

Deliver measurable outcomes within your assigned operations pillar by architecting systems that enable rapid school expansion with uncompromising quality, efficiency, and AI-enhanced precision.

Basic Requirements

• North America-based with capacity for 10-40% travel as operations demand
• 5+ years of proven performance in high-autonomy operations leadership
• Demonstrated proficiency with AI tools for research, documentation, problem-solving, and workflow automation
• Exceptional analytical capability and written communication skills
• Action-oriented mindset with high ownership and minimal ego
• Specialized experience in at least one core domain: permitting, construction management, educational technology systems, financial planning & analysis, or vendor management
• Working knowledge of operational platforms such as Klair, Syft, Wrike, Retool, or comparable low-code environments
• Proven ability to rapidly master new domains (legal frameworks, financial systems, compliance requirements)

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 a 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.

Working with Us

This is a full-time (40 hours per week), long-term position. You will enter into an independent contractor agreement with Crossover as a Contractor of Record. Compensation is $100 USD/hour, equating to $200,000 USD/year, with weekly payments. For details, visit www.crossover.com/help-and-faqs.

Legal and Job Codes

Crossover Job Code: LJ-5461-US-Baltimor-DirectorofOper1.001

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