Program Director, 2 Hour Learning @ Trilogy
Your Application Journey
Email Hiring Manager
Job Details
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performance and significant growth in student outcomes, the focus is on talent and robust performance rather than outdated methods.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
How to Get Hired at Trilogy
🎯 Tips for Getting Hired
- Customize your resume: Tailor experience to AI and EdTech.
- Highlight leadership: Emphasize program management successes.
- Showcase negotiation skills: Detail vendor selection achievements.
- Prepare for data questions: Be ready with performance insights.