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

Ready to transform education with real control and authority? This isn't just another program management role.

At 2 Hour Learning, we're revolutionizing education through AI-acceleration - compressing a full school day into just two hours while maintaining exceptional learning outcomes. Our audacious goal: help students learn twice as much in half the time. To achieve this, we need someone extraordinary to build and operate our execution system with precision and speed.

As our Program Director, you'll command an AI-powered control system for a $50M EdTech portfolio. Forget passive reporting - you'll create dynamic dashboards that eliminate meetings, develop vendor scorecards that drive real consequences, negotiate ironclad contracts, and oversee a meticulous bid process for every initiative. Each deliverable you manage directly impacts academic success, and your decisions determine which partnerships thrive or end.

If you're frustrated with creating presentations that gather dust and crave the power to directly influence student learning outcomes through decisive vendor management and execution excellence, this role offers the authority, urgency, and impact you've been seeking.

What You Will Be Doing

• Architect and manage a comprehensive AI-enhanced execution dashboard tracking 25+ concurrent initiatives to ensure maximum visibility, accountability and measurable outcomes
• Develop and implement data-driven vendor evaluation systems with clear performance metrics that trigger specific actions - from expanded responsibilities to contract termination
• Spearhead rigorous competitive vendor selection processes for all new initiatives, complete with defined scopes, budgets, and transparent award justifications
• Craft and secure airtight contracts featuring enforceable terms, performance incentives, and billing safeguards that eliminate ambiguity
• Produce decisive memos identifying vendor performance issues, documenting contract breaches, and recommending clear actions: termination, renegotiation, or executive escalation
  
  

What You Won’t Be Doing

• Serving as a mere coordinator - you'll have genuine authority and accountability, not just process templates
• Allowing vendor issues to languish - your role demands proactive problem identification with immediate escalation, resolution, or replacement
• Tolerating vague contractual language, missed deadlines, or imprecise billing practices
• Generating passive status reports without corresponding action plans
• Outsourcing AI utilization - you'll directly leverage AI tools as an essential component of your effectiveness
  
  

Program Director Key Responsibilities

Design, implement and oversee a comprehensive execution framework that ensures vendor accountability, optimizes resource allocation, and guarantees timely, high-quality deliverables across our $50M EdTech portfolio - ultimately driving measurable improvements in student learning outcomes.

Basic Requirements

• Minimum 5 years of leadership experience in Program Management, Portfolio Management, or PMO oversight managing multifaceted initiative portfolios
• Demonstrated success managing $25M+ technology budgets, including vendor selection processes, financial controls, and delivery supervision
• Substantial experience conducting competitive procurement processes and negotiating performance-based contracts with enforceable terms
• Track record of creating and maintaining AI-enhanced execution dashboards (using platforms like Linear, Jira, or Notion) that executives rely on for strategic decision-making, not merely progress tracking
• Proficient daily user of AI productivity tools (such as GPT, Copilot, and analytical dashboards) to streamline workflows, extract insights, and expedite deliverables
• Demonstrated capacity to achieve results in unstructured environments by independently solving problems, appropriately escalating issues, and taking ownership in high-pressure, ambiguous situations
• Exceptional executive communication abilities with proven history of influencing C-level decisions through compelling memos, intuitive dashboards, and rigorous vendor oversight
• Based in the US, willing to travel domestically up to 25%, and authorized to work in the US without requiring sponsorship
  
  

Nice-to-have Requirements

• Previous experience establishing or transforming a Program Management Office or operational control system
• Knowledge of educational technology platforms or metrics for measuring academic achievement
• Background in legal aspects, procurement processes, or contract management within technology environments
  
  

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-Colorado-ProgramDirecto.007