Program Director, 2 Hour Learning

@ Trilogy

About the Role

At 2 Hour Learning, part of Trilogy, we are transforming education through relentless execution and AI-powered innovation. The Program Director will architect and command a $50M EdTech portfolio, deploying an AI-enhanced execution system to drive real-time performance, vendor evaluations, and actionable insights.

What You Will Be Doing

• Spearhead our AI execution dashboard across 25+ initiatives.
• Design and implement cutting-edge vendor evaluation systems.
• Lead high-stakes vendor selection with precision.
• Craft bulletproof contracts tied to student outcomes.
• Author executive-level recommendations to trigger action.

What You Won’t Be Doing

• Playing a passive coordinator role.
• Allowing issues to grow unchecked.
• Settling for mediocre contracts or management.
• Creating reports that lack actionable insights.
• Remaining on the sidelines of AI innovation.

Program Director Key Responsibilities

Design, implement, and operate a state-of-the-art execution framework ensuring accountability, optimized resource allocation, and exceptional results across our EdTech ecosystem.

Basic Requirements

• 5+ years in program or portfolio management at scale.
• Experience managing $25M+ technology investments.
• Proven negotiator with competitive vendor selection skills.
• Expertise in building AI execution dashboards (Linear, Jira, Notion)
• AI power user with tools like GPT and Copilot.
• Strong strategic problem-solving ability in ambiguous environments.
• Compelling communicator influencing C-suite decisions.
• US-based professional, willing to travel 25% domestically.

Nice-to-have Requirements

• Success in PMO transformation or control system implementation.
• Working knowledge of EdTech platforms and academic performance metrics.
• Background in legal, procurement, or contract management.

About 2 Hour Learning

2 Hour Learning is reinventing the education model with AI-driven personalized learning. With top national performance and significant growth in student outcomes, the focus is on talent and robust performance rather than outdated methods.

Working with Us

This full-time position is offered on an independent contractor basis via Crossover. Compensation is $200 USD/hour, equating to $400,000 USD/year based on a 40-hour week over 50 weeks annually. Immediate availability is required.

Key Skills/Competency

• Program Management
• Portfolio Management
• AI Execution
• Vendor Negotiation
• Contract Management
• Strategic Thinking
• Data Analytics
• Leadership
• EdTech
• Execution Framework