Head of Program Management, 2 Hour Learning (Remote) - $400,000/year USD

Ready to transform education through ruthless execution excellence? At 2 Hour Learning, we're not just managing projects – we're revolutionizing how students learn through AI-powered efficiency. We're on a mission to compress a full day of learning into two hours, and we need a strategic powerhouse to architect our success.

If you've mastered the art of portfolio management but yearn for true autonomy and impact, this is your moment. We're seeking a visionary leader to build and command an AI-enhanced control system for our $50M EdTech portfolio. Forget passive reporting and endless meetings – you'll create dynamic dashboards that drive decisions, craft vendor agreements that demand excellence, and build systems that transform education.

This role combines strategic oversight with tactical precision. You'll be the architect of accountability, wielding both AI tools and business acumen to ensure every dollar spent advances our mission. When vendors fall short, you'll be empowered to act. When opportunities arise, you'll be positioned to seize them.

If you're ready to move beyond traditional program management into a role where your decisions directly impact educational outcomes, where automation replaces bureaucracy, and where your strategic vision becomes operational reality – welcome to your next challenge.

What You Will Be Doing

• Architect and maintain an AI-enhanced command center tracking 25+ initiatives in real-time, turning data into actionable insights
• Design and implement performance-based vendor evaluation systems that drive accountability and excellence
• Spearhead vendor selection processes with military precision, ensuring every partnership aligns with our mission and delivers value
• Craft ironclad contracts that protect our interests and incentivize outstanding performance
• Author decisive action memos that cut through ambiguity and drive strategic changes in vendor relationships
  
  

What You Won’t Be Doing

• Playing a passive coordination role – you're the decision-maker, not just a facilitator
• Watching problems grow – your mandate is to identify, address, and resolve issues proactively
• Accepting mediocrity in contracts, timelines, or financial management
• Creating reports that gather dust – every analysis drives action
• Outsourcing AI implementation – you'll be hands-on with cutting-edge technology
  
  

Head Of Program Management Key Responsibilities

Build, operate, and continuously improve a state-of-the-art execution framework that ensures vendor excellence, optimal resource allocation, and timely delivery across our $50M EdTech ecosystem.

Basic Requirements

• Demonstrated 5+ year track record of excellence in Program/Portfolio Management or PMO leadership
• Proven success managing $25M+ technology portfolios with full budget and vendor oversight
• Expert-level experience in competitive procurement and contract negotiation
• Mastery of AI-enhanced project management tools with a focus on executive-level reporting
• Demonstrated proficiency with AI tools for workflow optimization and analysis
• Track record of autonomous problem-solving and decisive action in complex environments
• Excellence in C-suite communication and influence through data-driven presentations
• Based in the US, willing to travel 25%, authorized to work without sponsorship
  
  

Nice-to-have Requirements

• Success stories in PMO establishment or transformation
• Knowledge of EdTech landscape and educational performance metrics
• Background in technology-focused legal or procurement operations
  
  

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-Allen-HeadofProgramM.004