Program Director, 2 Hour Learning (Remote) - $400,000/year USD

Ready to transform from portfolio manager to portfolio architect? At 2 Hour Learning, we're not just tracking progress—we're redefining it.

Our revolutionary AI-accelerated learning platform is condensing a full day's education into just two hours while maintaining exceptional academic outcomes. We're on a mission to help students learn twice as much in half the time, and we need a strategic orchestrator to build the execution framework that powers this transformation.

This role transcends traditional program management—it's about creating an AI-driven performance ecosystem that delivers measurable results. You'll design and implement the control system for a $50M EdTech portfolio where dashboards replace meetings, vendor performance directly impacts resource allocation, and every initiative ties back to student success.

If you're ready to move beyond creating presentations that gather dust and instead wield real decision-making authority with vendors, tools, and execution strategies that drive educational breakthroughs, this is your opportunity to make an impact at the speed of innovation.

What You Will Be Doing

• Architecting and maintaining an AI-enhanced execution dashboard ecosystem that provides real-time visibility across 25+ concurrent initiatives
• Developing data-driven vendor evaluation frameworks that trigger decisive action—from expanded partnerships to contract termination
• Spearheading competitive selection processes for new initiatives with crystal-clear parameters, budget frameworks, and decision criteria
• Crafting ironclad contracts with performance metrics, accountability mechanisms, and financial safeguards
• Authoring executive-level decision documents that identify vendor performance gaps, reference contractual obligations, and recommend specific interventions
  
  

What You Won’t Be Doing

• Serving as a passive coordinator—your role carries decision-making authority, not just administrative responsibility
• Waiting for problems to become crises—you'll identify issues early, intervene decisively, and drive resolution
• Tolerating vague deliverables, missed deadlines, or financial uncertainty in vendor relationships
• Creating status updates without corresponding action plans
• Outsourcing AI integration—you'll personally leverage AI tools to enhance program effectiveness
  
  

Program Director Key Responsibilities

Design, implement, and operate a comprehensive execution framework that ensures vendor accountability, optimizes resource allocation, and guarantees timely, high-quality deliverables across our $50M educational technology portfolio.

Basic Requirements

• Minimum 5 years' experience in senior Program Management, Portfolio Management, or PMO leadership overseeing multifaceted initiative portfolios
• Demonstrated management of $25M+ technology investments, including vendor selection, budget stewardship, and delivery accountability
• Substantial expertise in managing competitive bidding processes and negotiating performance-based contracts
• Track record of creating and maintaining AI-enhanced execution platforms (Linear, Jira, Notion) that inform executive decision-making—beyond basic progress tracking
• Proficient daily application of AI solutions (GPT, Copilot, analytics dashboards) to streamline workflows, extract insights, and expedite deliverables
• Demonstrated success driving outcomes in uncharted territory—resolving complex challenges, elevating critical issues, and taking ownership in ambiguous, high-pressure environments
• Exceptional executive communication capabilities, with proven success influencing C-suite decisions through strategic documentation, visual analytics, and vendor management
• Based in the US, willing to travel domestically up to 25%, and authorized to work in the US without sponsorship
  
  

Nice-to-have Requirements

• Previous leadership in establishing or transforming a PMO or operational control framework
• Knowledge of educational technology ecosystems or academic performance metrics
• Background in legal aspects, procurement processes, or contract management within technology sectors
  
  

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-5564-US-Baltimor-ProgramDirecto.002