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

Head of AI Operations, 2 Hour Learning (Remote) - $200,000/year USD

This range is provided by Trilogy. Your actual pay will be based on your skills and experience — talk with your recruiter to learn more.

Base pay range

$100.00/hr - $100.00/hr

Operations isn't a support function—it's our competitive advantage. At 2 Hour Learning, we're building a revolutionary network of AI-native K-12 schools where operational excellence directly drives expansion velocity. Our Operations Team stands at the forefront of our growth, with each team member becoming a specialized domain expert through hands-on implementation and AI-enhanced skill development across five critical areas:

• Authorization & Permitting – Navigate complex regulatory landscapes to secure multi-state approvals and expedite local permitting processes, unlocking new markets with precision.
• Physical Build-Out & Maintenance – Transform spaces into learning environments through oversight of construction, upgrades, and vendor relationships.
• Operational Setup – Ensure flawless school launches with perfectly configured systems—from devices to platforms to compliance frameworks.
• Financial Operations – Architect budgetary frameworks, develop real-time financial dashboards, and maintain financial controls across our expanding network.
• PMO – Drive critical tech and marketing initiatives through vendor management, progress tracking, and reporting.

Your impact will be immediate and tangible: crafting financial dashboards, designing onboarding systems, expanding into new regulatory territories, launching campuses rapidly, or creating AI workflows to revolutionize management. This is execution at its highest level—for builders who thrive on solving complex challenges.

If you instinctively build solutions rather than schedule discussions when facing obstacles, you'll excel here. Your systems will power our expansion of 25-30 new schools in the coming year, impacting hundreds of staff and thousands of students. Your results will tell the story of your success.

What You Will Be Doing

• Taking full ownership of a critical operations domain: Authorization, Build-Out, Setup, Finance, or PMO
• Pioneering innovative solutions within your domain through AI integration, automation strategies, and continuous improvement cycles
• Developing comprehensive specifications, interactive dashboards, and scalable operational playbooks for the expanding network
• Navigating and optimizing real-world operational constraints including vendor relationships, regulatory requirements, technical systems, and staff capabilities
• Engaging in strategic campus visits to implement solutions and validate their effectiveness in real educational environments

What You Won't Be Doing

• Passively waiting for technical teams to build tools—you'll create prototypes and automation solutions independently
• Taking shortcuts with AI-based documentation—you'll develop nuanced, field-tested solutions with measurable results
• Working exclusively from headquarters—regular travel and on-the-ground responsibilities are expected
• Creating strategies for others to execute—you'll own the full solution lifecycle from conception through implementation

Head Of AI Operations Key Responsibilities

Own and drive exceptional outcomes within your specialized operations pillar by architecting, implementing, and refining systems that enable rapid school expansion while maintaining standards of quality, efficiency, and AI-enhanced precision.

Basic Requirements

• North American residency with the ability to travel 10-40% as required
• Minimum 5 years of experience in high-velocity, self-directed operational roles
• Demonstrated proficiency leveraging AI tools for research, content creation, complex problem-solving, and workflow automation
• Exceptional analytical abilities and written communication skills
• Action-oriented mindset with low ego and high accountability
• Specialized experience in at least one core domain: permitting processes, construction management, educational technology systems, financial planning & analysis, or vendor relationship management
• Working knowledge of productivity and operational platforms such as Klair, Syft, Wrike, Retool, or similar low-code environments
• Proven ability to rapidly master new domains (legal frameworks, financial systems, compliance requirements, etc.)

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. Students are ranked highly nationally, and the program emphasizes talent and performance. The environment supports both on-campus and remote work for innovators, educators, and AI specialists focused on 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. 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, equating to $200,000 USD/year assuming 40 hours/week and 50 weeks/year. The payment period is weekly. For details, consult www.crossover.com/help-and-faqs.

Crossover Job Code: LJ-5461-US-Boston-HeadofAIOperat

Seniorities and locations: Boston, MA; Seniority level: Director; Employment type: Full-time

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