VP of Real Estate, 2 Hour Learning (Remote) - $...
This position places you at the center of site acquisition for one of America's fastest-expanding private school networks.
Your mandate is to source locations, negotiate lease terms, and manage broker networks across multiple markets, property types, and campus sizes (ranging from 25 to 1000 students) with both speed and accuracy. This is not a coordination or oversight position. You will personally identify, evaluate, and close sites across diverse asset classes, with genuine decision authority and no bureaucratic delays.
2 Hour Learning is establishing a national network of schools, and this position is the key that unlocks that expansion by building a scalable, repeatable site sourcing and launch engine. You will enable campus openings by securing high-caliber sites and executing lease agreements with consistency, velocity, and scale. The organization requires someone capable of rendering weekly go/no-go decisions, finalizing transactions in days rather than weeks, and mobilizing broker networks to generate qualified opportunities. You will leverage AI tools to surpass the pace of conventional real estate teams.
If you view real estate transactions as a competitive discipline and are motivated to succeed across markets, formats, and deadlines, this opportunity is designed for you.
What You Will Be Doing
Take full ownership of the campus site sourcing pipeline from end to end, encompassing the definition of viability standards, management of broker networks, and personal execution of lease closings that dictate the pace and geography of our growth.
Basic Requirements
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 They’re tearing down the outdated one-size-fits-all model and replacing it with AI-driven personalized learning that helps kids master academics in just two hours a day.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-5736-US-Chicago-VPofRealEstate.001
Apply Now
Your mandate is to source locations, negotiate lease terms, and manage broker networks across multiple markets, property types, and campus sizes (ranging from 25 to 1000 students) with both speed and accuracy. This is not a coordination or oversight position. You will personally identify, evaluate, and close sites across diverse asset classes, with genuine decision authority and no bureaucratic delays.
2 Hour Learning is establishing a national network of schools, and this position is the key that unlocks that expansion by building a scalable, repeatable site sourcing and launch engine. You will enable campus openings by securing high-caliber sites and executing lease agreements with consistency, velocity, and scale. The organization requires someone capable of rendering weekly go/no-go decisions, finalizing transactions in days rather than weeks, and mobilizing broker networks to generate qualified opportunities. You will leverage AI tools to surpass the pace of conventional real estate teams.
If you view real estate transactions as a competitive discipline and are motivated to succeed across markets, formats, and deadlines, this opportunity is designed for you.
What You Will Be Doing
- Establish and iteratively refine site viability frameworks that address zoning, permitting, square footage requirements, demographic fit, brand standards, and regulatory exposure, then convert these frameworks into AI-compatible formats that support automated filtering and prioritization
- Render decisive go/no-go determinations on prospective sites each week, informed by research conducted by individual contributors and brokers, and advance the pipeline with clear reasoning tied to viability standards
- Personally negotiate and finalize term sheets, letters of intent, and lease revisions through to execution, balancing transaction speed, risk exposure, and financial terms, while deploying AI tools to identify clause-level concerns and expedite legal assessment
- Develop high-context collateral and conduct regular briefings to engage brokers, developers, and investors. Apply AI to create tailored updates at scale that generate qualified deal flow
- Building or overseeing a large team or handing off deal execution to subordinates
- Concentrating on long-range strategic initiatives at the expense of weekly progress and real-time deal closure
- Facilitating transactions without direct accountability for results, from initial prospect through signed lease
Take full ownership of the campus site sourcing pipeline from end to end, encompassing the definition of viability standards, management of broker networks, and personal execution of lease closings that dictate the pace and geography of our growth.
Basic Requirements
- 5+ years of experience leading multi-site real estate expansion initiatives or site sourcing programs
- Personal track record of closing a minimum of 25 commercial real estate transactions, including leases and/or acquisitions, with direct responsibility for deal structure and execution
- Proven ownership of transaction outcomes, not merely coordination or supervisory involvement
- Active use of AI tools in day-to-day work (e.g., GPT, clause analysis, research, pipeline tracking)
- Capability to rapidly assess site viability through evaluation of zoning, permitting, and regulatory environments
- Proficiency with AI tools for research, document drafting, and contract review
- U.S.-based and able to travel up to 25%
- Legally authorized to work in the U.S. without requirement for sponsorship
- Experience in franchise expansion or multi-unit retail deployment
- Track record of developing or substantially enhancing repeatable site selection frameworks
- Demonstrated capability to assess lease versus purchase trade-offs and determine the optimal structure for each site
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-5736-US-Chicago-VPofRealEstate.001
Apply Now