Job Description

Overview Elite Program Directors don't manage projects. They architect systems that transform ambitious vision into measurable reality. At 2 Hour Learning, we're revolutionizing education with a bold promise: students learn twice as much in just two hours a day. Behind this outcome lies a sophisticated $50M EdTech portfolio that demands exceptional leadership. We need the architect who will build our execution layer—the operating system that drives alignment, optimization, and relentless focus on outcomes across our entire organization. You'll create the structure, systems, and standards that bring unprecedented visibility, accountability, and velocity across 25+ high-impact initiatives. Your work will influence whether we invest in what actually delivers results. From defining performance metrics to enforcing competitive vendor processes to building AI-powered reporting systems, your architecture will shape strategy and surface truth. Working directly with founders, you'll translate our ambitious vision into disciplined execution. If you excel in complexity, thrive on autonomy, and demand measurable impact—this rare opportunity is designed specifically for you. What You Will Be Doing Architecting and implementing a centralized, AI-driven PMO that transforms how we oversee and optimize 25+ EdTech initiatives across our $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 using advanced tools like Linear 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 Program Director Key Responsibilities Architect and lead a data-driven, AI-powered PMO that transforms a $50M EdTech portfolio into measurable academic outcomes at unprecedented speed and efficiency. Basic 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. With students consistently ranking in the top 1-2% nationally and the top 20% achieving a 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 part of fixing a broken school system. 2 Hour Learning is reprogramming learning for the AI era. 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 for more details on this topic. #J-18808-Ljbffr Trilogy

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