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Crossover

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

Crossover, Washington, District of Columbia, us, 20022

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Director of Operations & Automation, 2 Hour Learning (Remote) Join to apply for the

Director of Operations & Automation, 2 Hour Learning (Remote)

role at

Crossover .

This role offers a base pay range of

$100.00/hr – $100.00/hr

and a total compensation potential of $200,000 USD per year. The position is full‑time (40 hours per week) and requires an independent contractor agreement with Crossover.

Operations Overview Operations is the backbone of everything we do. At 2 Hour Learning, our AI‑native K‑12 School Network scales only if our operational infrastructure scales with it. The Operations Team doesn’t assist growth—they enable it.

Authorization & Permitting – Obtain multi‑state legal clearance and expedite local permits to open new markets.

Physical Build‑Out & Maintenance – Manage campus construction, facility improvements, and vendor accountability to deliver and maintain exceptional learning environments.

IT Operational Setup – Ensure every new campus launches with full system readiness—hardware, software, support infrastructure, and compliance—on day one.

Financial Operations – Create budgets, generate real‑time insight dashboards, and ensure audit‑grade financial oversight across all schools and business units.

PMO – Drive execution of critical technology and marketing projects through vendor performance tracking, reporting dashboards, and initiative management.

What You Will Be Doing

Leading one of five foundational operations domains: Authorization, Build‑Out, Platforms, Finance, or PMO.

Addressing novel challenges in your domain through AI, automation, and fast experimentation.

Creating clear documentation, dashboards, or process guides that work at multi‑campus scale.

Engaging with operational realities: facility vendors, regulatory bodies, technical systems, and campus teams.

Visiting school sites when necessary to deploy or validate your operational solutions.

What You Won’t Be Doing

Waiting for product or engineering teams to build operational tools—you’ll prototype and automate independently.

Asking AI to “generate a standard operating procedure” and considering the work finished—you’ll vibe‑code functional solutions.

Operating exclusively from headquarters—expect regular travel and on‑campus delivery.

Delegating execution of your strategy to others—you’ll own both planning and implementation.

Key Responsibilities Deliver results within your designated operations pillar by creating scalable systems that enable rapid school expansion with precision, efficiency, and AI‑first methodology.

Basic Requirements

Located in North America with flexibility to travel 25‑75% as required.

5+ years in a high‑velocity, high‑autonomy operations environment.

Excellent analytical capabilities and written communication.

Action‑oriented mindset, minimal ego, strong sense of ownership.

Background in one of these areas: regulatory compliance, facilities construction, SaaS user onboarding, FP&A, or technology vendor management.

Leverages AI with the same fluency others apply to spreadsheets: reflexively, often, and across diverse scenarios.

Has created automations, systematized processes, and explored vibe‑coding for productivity or personal interest.

Demonstrated ability to master new domains quickly (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 6.5× 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.

Working with us 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!

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