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

You’ll never be “just ops” here.

At 2 Hour Learning, Operations Is The Product. Our National Network Of AI-native K-12 Schools Only Works If Our Campus Systems Do. That’s Why Our Operations Team Doesn’t “support” Expansion; They Drive It. Each Person Operates In One Of Five Mission-critical Domains, Becoming a Domain Expert Fast Through Real-world Immersion And AI-accelerated Learning

• Authorization & Permitting – Secure multi-state legal approval and fast-track local permitting to unlock new markets.
• Physical Build-Out & Maintenance – Oversee campus construction, upgrades, and vendor performance to deliver and sustain high-quality facilities.
• IT Operational Setup – Launch every new school with all systems—devices, platforms, support, compliance—fully configured and ready to go.
• Financial Operations – Build budgets, deliver daily insight dashboards, and maintain audit-ready financial control across every school and vertical.
• PMO – Accelerate delivery of key tech and marketing initiatives through vendor scorecards, dashboards, and initiative-level reporting.
  
  

You’ll ship dashboards that clarify financial blind spots. Design onboarding systems that halve student setup errors. Secure regulatory approval in new states. Stand up campuses in record time. Or prototype AI-first workflows that replace layers of traditional management. This is high-stakes, high-velocity execution—done by builders, not bystanders.

If you're the kind of operator who sees bottlenecks and starts building—not scheduling meetings—you'll thrive here. Your systems will power the next 25–30 schools we open in the next year. Your work will define what great looks like for hundreds of staff and thousands of students. And your track record will speak for itself.

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 Won’t Be Doing

• Waiting for product or engineering to build your ops tools—you’ll prototype or automate yourself
• Asking AI to “write an SOP” and calling it a day—you’ll vibe-code solutions that actually work
• Being siloed in a central office—expect to travel and ship on-site outcomes
• Handing off your strategy to someone else to execute—you’ll 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 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 an astonishing 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.

Here’s How They’re Fixing It.

There is so much to cover for this exciting role, and space here is limited. Hit the Apply button if you found this interesting and want to learn more. We look forward to meeting you!

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.

Crossover Job Code: LJ-5461-US-Denton-HeadofAIOperat.005