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

You've managed portfolios worth over $25 million. You've crafted dashboards, raised issues, and attended countless meetings. But have you ever had the reins in your hands?

At 2 Hour Learning, you will. We're on a mission to revolutionize education by compressing a full school day into just two hours with AI-driven efficiency. Our goal is ambitious: to help students learn twice as much in half the time. To achieve this, we need an execution system that matches our speed and ambition, and you'll be the architect behind it.

This role goes beyond traditional project management; it's about performance control. You'll design and manage an AI-driven control system for a $50 million EdTech portfolio. Forget meetings—live dashboards will be your new norm. You'll develop vendor scorecards that lead to strategic decisions—whether that's reallocating resources, replacements, or terminations. You'll be the one negotiating and enforcing contracts, and every new project will pass through your rigorous vetting process. Every deliverable will be tied to academic impact, and if a vendor falls short, your decisive memos will set the course of action.

Our pace is rapid, our processes automated, and our tolerance for passivity non-existent. If you're weary of creating presentations that gather dust and eager to take charge of the tools, vendors, and execution outcomes that truly impact student learning, you'll find the authority and urgency you seek here.

What You Will Be Doing

• Lead the charge with a dynamic, AI-driven execution dashboard overseeing 25+ initiatives—ensuring transparency, responsibility, and impactful results.
• Create rubric-based vendor scorecards that drive decisions: expand work, reduce scope, replace, or terminate.
• Conduct structured and competitive vendor evaluations for every new project—defining precise scopes, budgets, and award justifications.
• Negotiate contracts with clear terms, aligned performance metrics, and billing safeguards—no room for ambiguity.
• Draft memos to highlight vendor shortcomings, point out contract breaches, and recommend decisive actions—whether it's offboarding, renegotiating, or escalating.
  
  

What You Won’t Be Doing

• Merely coordinating—this role involves leadership, not just templates.
• Allowing vendor issues to "bubble up"—you'll escalate, resolve, or replace.
• Accepting vague contracts, missed milestones, or uncertain billing.
• Writing passive reports with no subsequent action.
• Leaving AI usage to analysts—this is a hands-on, AI-integrated position.
  
  

Program Management Officer Key Responsibilities

Design and manage the execution system that enforces vendor accountability, reallocates resources, and ensures timely, high-quality delivery across a $50 million EdTech portfolio.

Basic Requirements

• Over 5 years in Program Management, Portfolio Management, or PMO leadership roles overseeing complex, multi-initiative portfolios.
• Proven track record in managing $25 million+ technology budgets, including vendor selection, budget control, and delivery oversight.
• Hands-on experience in running competitive bid processes and negotiating enforceable contracts.
• Experience in building and operating AI-driven execution dashboards (Linear, Jira, Notion) utilized by executives for decision-making, not just tracking.
• Daily user of AI tools (e.g., GPT, Copilot, dashboards) to automate tasks, synthesize insights, and expedite delivery.
• Demonstrated ability to achieve outcomes without predefined guidelines—solving problems, escalating issues, and taking ownership in high-ambiguity, high-stakes situations.
• Strong executive communication skills, with a history of influencing C-suite decisions through memos, dashboards, and vendor management.
• Based in the US, willing to travel domestically up to 25%, and eligible to work in the US without sponsorship.
  
  

Nice-to-have Requirements

• Experience in launching or revamping a PMO or control system.
• Understanding of education tech platforms or academic outcome metrics.
• Exposure to legal, procurement, or contract governance in tech 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-Aurora-ProgramManagem.002