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

Join to apply for the Program Director, 2 Hour Learning (Remote) - $400,000/year USD role at Trilogy 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 #J-18808-Ljbffr

Created: 2025-09-17