What are the responsibilities and job description for the Program Management Officer, 2 Hour Learning (Remote) - $400,000/year USD position at Crossover?
You've mastered the art of portfolio management. You've created dashboards that impress, navigated complex issues, and endured countless meetings. But true control has remained elusive—until now.
At 2 Hour Learning, we're revolutionizing education through AI-acceleration. Our audacious goal? Compress an entire school day into just two hours while maintaining excellence in learning outcomes. We're building a system where students learn twice as much in half the time, and we need a strategic architect to construct the execution framework that matches our velocity.
This role transcends traditional project management—it's about performance control at its core. You'll design and implement an AI-driven control system for a $50M EdTech portfolio that replaces meetings with actionable dashboards, transforms vendor relationships through rigorous scorecards, and enforces contracts with precision. Every initiative passes through your evaluation process, every deliverable connects directly to student success, and your decisive recommendations determine vendor futures.
We value speed, automation, and proactive leadership. If you're ready to move beyond creating presentations that gather dust and instead wield real authority over tools, vendors, and outcomes that directly impact educational achievement, you'll find the empowerment, responsibility, and momentum you've been searching for with us.
What You Will Be Doing
Architect and implement the comprehensive execution framework that ensures vendor accountability, optimizes resource allocation, and guarantees timely, superior deliverables across a $50M EdTech portfolio—directly influencing educational outcomes through operational excellence.
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 They’re tearing down the outdated one-size-fits-all model and replacing it with AI-driven personalized learning that helps kids master academics in just two hours a day.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-5564-US-Aurora-ProgramManagem.007
At 2 Hour Learning, we're revolutionizing education through AI-acceleration. Our audacious goal? Compress an entire school day into just two hours while maintaining excellence in learning outcomes. We're building a system where students learn twice as much in half the time, and we need a strategic architect to construct the execution framework that matches our velocity.
This role transcends traditional project management—it's about performance control at its core. You'll design and implement an AI-driven control system for a $50M EdTech portfolio that replaces meetings with actionable dashboards, transforms vendor relationships through rigorous scorecards, and enforces contracts with precision. Every initiative passes through your evaluation process, every deliverable connects directly to student success, and your decisive recommendations determine vendor futures.
We value speed, automation, and proactive leadership. If you're ready to move beyond creating presentations that gather dust and instead wield real authority over tools, vendors, and outcomes that directly impact educational achievement, you'll find the empowerment, responsibility, and momentum you've been searching for with us.
What You Will Be Doing
- Developing and maintaining an AI-enhanced execution dashboard tracking 25 concurrent initiatives to drive transparency, responsibility, and measurable results.
- Creating evidence-based vendor evaluation systems that prompt decisive action—whether expanding collaboration, reducing scope, seeking alternatives, or terminating relationships.
- Orchestrating methodical, competitive vendor selection processes for all new projects—establishing definitive scopes, budgets, and selection justifications.
- Crafting and securing contracts with ironclad terms, performance metrics, and financial safeguards—eliminating ambiguity and vulnerabilities.
- Authoring decisive recommendations that identify vendor shortcomings, reference specific contract breaches, and propose clear courses of action—whether termination, renegotiation, or escalation.
- Merely facilitating rather than taking ownership—this position carries authority, not just administrative responsibilities.
- Waiting for vendor issues to become crises—you'll identify, address, or replace proactively.
- Tolerating vague contractual language, missed deadlines, or financial uncertainties.
- Generating status reports without corresponding action plans.
- Outsourcing AI utilization—you'll personally leverage AI tools as core components of your effectiveness.
Architect and implement the comprehensive execution framework that ensures vendor accountability, optimizes resource allocation, and guarantees timely, superior deliverables across a $50M EdTech portfolio—directly influencing educational outcomes through operational excellence.
Basic Requirements
- Minimum 5 years of experience in Program Management, Portfolio Management, or PMO leadership coordinating diverse, multi-faceted initiative portfolios
- Demonstrated management of $25M technology investments, encompassing vendor evaluation, budget administration, and implementation supervision
- Direct experience conducting competitive procurement processes and securing advantageous, enforceable contractual agreements
- Track record of creating and maintaining AI-enhanced execution dashboards (Linear, Jira, Notion) that executives rely on for strategic decisions—beyond basic progress monitoring
- Proficient daily application of AI technologies (e.g., GPT, Copilot, analytics platforms) to streamline workflows, extract meaningful insights, and expedite project completion
- Demonstrated capacity to deliver results without established frameworks—resolving challenges, elevating critical issues, and assuming responsibility in complex, high-pressure environments
- Exceptional executive communication capabilities, with proven success influencing C-level decisions through compelling documentation, visual analytics, and vendor management
- Based in the United States, willing to travel domestically up to 25%, and authorized to work in the US without requiring sponsorship
- Previous leadership in establishing or transforming a PMO or operational control system
- Knowledge of educational technology platforms or academic performance measurement systems
- Background in legal aspects, procurement processes, or contract management within technology sectors
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.007
Salary : $400,000