Job Details

Overview

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.

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

What You Will Be Doing

• Owning one of five core ops pillars: Authorization, Build-Out, Platforms, Finance, or PMO
• Solving first-time problems in your pillar using AI, automation, and rapid iteration
• Writing clear specs, dashboards, or runbooks that scale across dozens of schools
• Interfacing with real-world constraints: campus vendors, regulators, systems, and staff
• Traveling to campuses when needed to implement or pressure-test your solutions

What You Wont Be Doing

• Waiting for product or engineering to build your ops toolsyoull prototype or automate yourself
• Asking AI to write an SOP and calling it a dayyoull vibe-code solutions that actually work
• Being siloed in a central officeexpect to travel and ship on-site outcomes
• Handing off your strategy to someone else to executeyoull do both, end-to-end

Head Of AI Operations Key Responsibilities

Own outcomes within your assigned operations pillar by building systems that support blitz-scale school expansion with speed, accuracy, and AI-native precision.

Basic Requirements

• Based in North America and able to travel 25-75% as needed
• 5+ years in a fast-paced, high-autonomy ops role
• Strong analytical and written communication skills
• Bias for action, low ego, high ownership
• Experience in one of the following: regulatory compliance, facilities buildout, SaaS user onboarding, FP&A, or tech vendor management
• Uses AI the way others use spreadsheets: instinctively, frequently, and across use cases
• Has built automations, systemized workflows, and experimented with vibe-coding for fun or efficiency
• Track record of rapid domain ramp-up (legal, finance, compliance, systems, etc.)

About 2 Hour Learning

Education is broken, but 2 Hour Learning is proving it doesnt have to be. Theyre tearing down the outdated one-size-fits-all model and replacing it with AI-driven personalized learning that helps kids master academics in just two hours a day.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, theyre proving that smarter learning is possible. At 2 Hour Learning, talent and performance matter. They offer a dynamic, on-campus and remote-friendly environment where innovators, educators, and AI specialists can be part of fixing a broken school system.

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.

We look forward to meeting you!