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Crossover

Director of Real Estate and Development, 2 Hour Learning (Remote) - $200,000/yea

Crossover, Hartford, Connecticut, United States

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Director of Real Estate and Development, 2 Hour Learning (Remote) – $200,000/year USD We are hiring a Director of Real Estate and Development to lead the launch of 2 Hour Learning facilities across the United States. The role is fully remote and is offered by Crossover.

Base pay range $100.00 per hour

About the role If you have managed the launch of a school, healthcare facility, or commercial site and want to leverage AI to accelerate permitting, this position is for you.

2 Hour Learning is scaling the fastest school model nationwide. Opening a new location relies on regulatory approvals—licenses, permits, and compliance filings. As Director, you will determine requirements, sequence submissions, and ensure timely approvals, using AI‑driven tools while also engaging directly with contractors, architects, and local officials.

You will work in a high‑velocity organization where speed and quality are mandatory. Your use of technology will cut through red tape to accelerate permitting cycles and deliver results.

What You Will Be Doing

Coordinate among architects, contractors, and legal counsel to obtain all necessary construction and operational permits for educational facilities.

Manage municipal permitting and inspection workflows across multiple jurisdictions, reducing timelines and removing obstacles.

Compile and file comprehensive approval packages—permits, applications, regulatory submissions, and inspection records.

Oversee project progress and compliance exposure across all sites—ensuring real‑time transparency and no unexpected delays.

Travel to project locations (~75%) to engage directly with local government officials, inspectors, and service providers to sustain momentum.

What You Won’t Be Doing

Wait for others to flag problems or finalize submissions—own full accountability for outcomes.

Operate solely from a central office—this is a field‑driven execution role.

Follow a rigid, one‑size‑fits‑all process by jurisdiction—design custom solutions as challenges arise.

Treat delays as unavoidable—both speed and accuracy define this position.

Depend on outdated systems or manual oversight—continuous automation and improvement are expected.

Basic Requirements

Located in the U.S. with authorization to work without visa sponsorship.

Willing and able to travel approximately 75% of the time to various U.S. cities and states.

5+ years directing permitting, construction, or facility expansion initiatives involving tangible assets and regulatory clearance.

5+ years coordinating multiple contractors per project across different jurisdictions.

Documented history of delivering projects ahead of schedule while maintaining full regulatory compliance.

Experience communicating project status to both technical teams and executive leadership.

Clear ownership track record—served as the central point of accountability for project execution and problem resolution.

AI‑native approach—deploy automation and iterative methods to accelerate delivery.

Written communication precise, actionable, and relied upon by senior leadership.

Strong regulatory judgment—know when to elevate, seek clarification, or challenge requirements.

Nice‑to‑have Requirements

Experience in construction management, educational operations, or multi‑location retail rollout.

Background developing or refining AI‑driven tools for permitting, compliance, or regulatory processes.

Previous collaboration with fire marshals, building inspectors, and educational licensing authorities.

About 2 Hour Learning Education is broken, but 2 Hour Learning is proving it doesn’t have to be. By tearing down the outdated one‑size‑fits‑all model, we’re building an AI‑driven personalized learning experience that helps kids master academics in just two hours a day. With students consistently ranking in the top 1‑2% nationally, we’re proving that smarter learning is possible.

We offer a dynamic, on‑campus and remote‑friendly environment for innovators, educators, and AI specialists who want to fix 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.

Seniority level Director

Employment type Full‑time

Job function Management, Engineering, and Project Management

Industries Construction, Education Administration Programs, Real Estate

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