Job Details

Overview

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

This range is provided by Trilogy. Your actual pay will be based on your skills and experience talk with your recruiter to learn more.

Base pay range

$200.00/hr - $200.00/hr

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 Wont 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 doesnt have to be. Theyre 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, theyre proving that smarter learning is possible. At 2 Hour Learning, its 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.

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.