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

Join to apply for the Head of AI Operations, 2 Hour Learning (Remote) - $200,000/year USD role at Trilogy.

Overview

Base pay range: $100.00/hr - $100.00/hr. This role leads the Operations function at 2 Hour Learning, focusing on AI-enabled operational excellence to support rapid campus expansion.

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 that function seamlessly across our expanding school 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

• Passive reliance on technical teams to build operational tools—you'll create prototypes and automation solutions independently
• Using generic AI documentation—you'll develop nuanced, field-tested solutions with measurable results
• Working exclusively from headquarters—travel and on-the-ground implementation are required
• Creating strategies for others to execute—you'll own the full solution lifecycle from concept to 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 quality, efficiency, and AI-enhanced precision.

Basic Requirements

• North American residency with ability to travel 10-40% as operational needs dictate
• 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 capabilities 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 comparable low-code development environments
• Proven ability to rapidly master new domains (legal frameworks, financial systems, compliance requirements, technical platforms, 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.

With students consistently ranking in the top 1-2% nationally and the top 20% achieving substantial growth, they're proving smarter learning is possible. 2 Hour Learning offers a dynamic, on-campus and remote-friendly environment where innovators, educators, and AI specialists can contribute to improving the school system.

Working with us

This is a full-time (40 hours per week), long-term position with independent contractor status through Crossover as Contractor of Record. The compensation level for this role is $100 USD/hour, equating to $200,000 USD/year with 40 hours/week and 50 weeks/year. The payment period is weekly. For details, see www.crossover.com/help-and-faqs.

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

Note: Referral opportunities and location details are included in the job posting.

Seniority level: Director. Employment type: Full-time. Job function: Engineering and Information Technology. Industries: Software Development, Education Administration Programs, and IT Services and IT Consulting.