Executive Director of Operations, 2 Hour Learning (Remote) - $400,000/year USD

Trilogy; United States; Remote; USD 200,000 - 400,000; Full time

Job summary

A leading company in educational innovation seeks an Executive Director of Operations to design AI-driven systems that enhance operational efficiency. This remote role demands a visionary leader with a solid background in operational management and a passion for transforming education through technology.

Qualifications

• 10+ years in operational leadership roles.
• Experience in a leading consulting firm like McKinsey, Bain, or BCG.
• Hands-on in building AI operations.

Responsibilities

• Design AI-driven operational systems.
• Transform data into actionable insights.
• Lead a cross-functional portfolio for systemic change.

Skills

AI-centered operational efficiency

Data transformation into strategies

Technical automation

Tools

Zapier

LangChain

Job description

Executive Director of Operations, 2 Hour Learning (Remote) - $400,000/year USD

Join to apply for the Executive Director of Operations, 2 Hour Learning (Remote) - $400,000/year USD role at Trilogy

Executive Director of Operations, 2 Hour Learning (Remote) - $400,000/year USD

Join to apply for the Executive Director of Operations, 2 Hour Learning (Remote) - $400,000/year USD role at Trilogy

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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

$200.00/hr - $200.00/hr

You've excelled in high-stakes operational roles, turning challenges into triumphs. Perhaps you've been a Chief of Staff or COO, but now you're seeking something more fulfilling.

Imagine owning systems without the red tape, creating scalable solutions that don't just stay on paper. You're ready to dive into the parts of the job that excite you the most. At 2 Hour Learning, we're growing a school model that boosts academic growth exponentially in just two hours daily. Join our elite team of senior operators, working closely with our founder. You'll own your portfolio, designing AI-driven operational systems that propel us forward.

This role isn't about flashy slides on AI transformation. It's about connecting systems, triggering APIs, and turning complexity into opportunity. If you've ever wanted a role that melds technical prowess with executive leadership, this is it.

What You Will Be Doing

• Designing and implementing AI-centric systems that elevate operational efficiency—taking charge from inception to iteration.
• Transforming data into actionable strategies—developing frameworks that provide real-time insights to the founder.
• Leading a cross-functional portfolio to drive systemic change across domains, without requiring additional headcount.
• Delivering high-impact solutions to the CEO and executing them swiftly.
• Utilizing your technical expertise to automate processes many leaders still conceptualize on whiteboards.
  
  

What You Won’t Be Doing

• Managing a team—this role is for builders, not for solving people puzzles.
• Proposing ideas you can't implement—you'll suggest solutions you know how to execute.
• Participating in governance reviews or alignment calls—your direct feedback loop is with the CEO.
• Discussing transformation without tools—you'll be hands-on with AI, not just talking about it.
• Overseeing campuses, curriculum, or teaching staff—this is about system-level operations.
  
  

Executive Director Of Operations Key Responsibilities

Develop and deploy AI-driven operational systems that support strategic growth, provide real-time insights to the founder, and enable consistent high-quality results at scale.

Basic Requirements

• 10+ years in operational leadership within multi-site sectors like education, retail, hospitality, or healthcare.
• Background at a leading consulting firm (McKinsey, Bain, or BCG)—capable of strategic high-level thinking.
• Hands-on experience in building AI-powered operations using tools such as Zapier, Make, LangChain, or custom automation solutions.
• Proven track record of turning operational challenges into scalable solutions and implementing them personally.
• Ability to extract executive-level insights from complex operational data.
• U.S.-based with a willingness to travel approximately 30% to campus locations.
• Authorized to work in the U.S. without visa sponsorship.
  
  

Nice-to-have Requirements

• Experience in scaling from startup to a multi-site organization, enabling 10x growth through infrastructure.
• Strong collaboration with product or engineering teams—especially if you've shipped features or integrated new platforms into operations.
• Proven ability to achieve more with fewer resources—favoring automation and leverage over processes.
• Acquaintance with K–12 education, high-end service operations, or customer-facing sectors where quality cannot be compromised at scale.
  
  

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 $200 USD/hour, which equates to $400,000 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-4410-US-COUNTRY-ExecutiveDirec.007

Seniority level

• Seniority level

  Executive

Employment type

• Employment type

  Full-time

Job function

• Job function

  Engineering, Project Management, and Strategy/Planning

• Industries

  Education Administration Programs, E-Learning Providers, and IT Services and IT Consulting

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