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

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Overview

Program Director role at Trilogy focusing on 2 Hour Learning. This position is remote and offers up to $400,000/year USD depending on skills and experience.

What You Will Be Doing

• Architecting and implementing a centralized, AI-driven PMO that transforms how we oversee and optimize 25+ EdTech initiatives across a $50M portfolio
• Developing and deploying a sophisticated vendor scorecard system that reallocates work based on objective performance data, eliminating subjective decision-making
• Designing and enforcing a rigorous dual-bid process for all new initiatives, ensuring maximum ROI and strategic alignment
• Building real-time tracking and reporting infrastructure to deliver executive-grade visibility across the entire portfolio
• Driving strategic alignment between internal stakeholders and vendors with clear accountability for timelines, documentation standards, and measurable academic outcomes

What You Won't Be Doing

• Managing static spreadsheets and manually collecting status reports; your systems will automate data collection and surface insights
• Spending valuable time with underperforming vendors; your performance framework will provide clear metrics and consequences
• Participating in information-gathering meetings; your dashboards will deliver real-time intelligence before conversations begin
• Operating a traditional PMO focused on compliance checkboxes; your system will drive measurable academic impact
• Working with ambiguous success metrics; you'll implement AI-powered systems that quantify academic value and ROI

Key Requirements

• 10+ years of proven experience in Program Management, Portfolio Management, or PMO Leadership, with demonstrated success overseeing large-scale, multi-initiative portfolios
• Verifiable track record managing $25M+ technology budgets with strategic allocation expertise and measurable ROI
• Advanced expertise in vendor management and contracting, including implementing competitive bidding systems, negotiating performance-based contracts, and optimizing vendor performance
• Demonstrated success implementing centralized tracking and reporting systems, preferably AI-driven (e.g., Linear, Jira, Asana, or similar platforms)
• Exceptional executive stakeholder management capabilities with proven ability to influence C-suite decision-making through data-driven insights
• Demonstrated experience leveraging AI for process automation and analytics to drive operational efficiency and strategic insights
• Must be based in North America

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.

2 Hour Learning is reprogramming learning for the AI era. They offer a dynamic, on-campus and remote-friendly environment where innovators, educators, and AI specialists can contribute to fixing a broken school system.

Here's how they're fixing it: hit the Apply button to learn more.

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. Compensation is $200 USD/hour ($400,000/year assuming 40 hours/week and 50 weeks/year). Payment is weekly.

Crossover Job Code: LJ-5564-US-Baltimor-ProgramDirecto.001