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

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

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

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. Our operations team drives expansion, becoming domain experts fast through real-world immersion and AI-accelerated learning.

What You Will Be Doing

• Owning one of six core ops pillars: Authorization, Build-Out, Setup, 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

Director Of Operations & Automation 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 10–40% as needed
• 5+ years in a fast-paced, high-autonomy ops role
• Proven use of AI tools for research, writing, problem-solving, and automation
• Strong analytical and written communication skills
• Bias for action, low ego, high ownership
• Experience in one of the following: permitting, construction, edtech systems, FP&A, or vendor mgmt
• Familiarity with tools like Klair, Syft, Wrike, Retool, or other low-code stacks
• 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 They're tearing down the outdated one-size-fits-all model and replacing it with AI-driven personalized learning that helps kids master academics in just two hours a day.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 a 6.5x growth, they're 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 fix a broken school system.

2 Hour Learning is reprogramming learning for the AI era. Here's how they're fixing it.

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. Compensation is $100 USD/hour, equating to $200,000 USD/year assuming 40 hours per week and 50 weeks per year. The payment period is weekly.

If you'd like to learn more, click Apply. We look forward to meeting you!

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