Program Director, 2 Hour Learning

@ Trilogy

Overview

At 2 Hour Learning, part of Trilogy, we are revolutionizing education with an AI-accelerated approach that compresses a full school day into two powerful hours. We are looking for a fearless Program Director to architect our ambitious vision and transform a $50M EdTech portfolio into a precision instrument of educational excellence.

What You Will Be Doing

As the Program Director, you will:

• Architect and command an AI-enhanced mission control dashboard with real-time insights for over 25 strategic initiatives.
• Design and implement data-driven vendor evaluation systems that reward excellence and eliminate underperformance.
• Spearhead vendor selection with rigorous competitive evaluations to optimize resource allocation.
• Craft ironclad contracts that align vendor incentives with educational outcomes.
• Author decisive action memos that translate performance data into strategic decisions.

What You Won’t Be Doing

• Playing a passive coordinator role - you will make executive decisions.
• Allowing problems to grow - you will take immediate, decisive action.
• Accepting mediocrity in contracts, timelines, or financial management.
• Creating reports that gather dust - every analysis drives action.
• Outsourcing AI expertise - you will be hands-on with cutting-edge technology.

Program Director Key Responsibilities

Execute and maintain a state-of-the-art performance control system that maximizes vendor accountability, optimizes resource allocation, and ensures exceptional delivery across our $50M EdTech ecosystem.

Basic Requirements

• 5+ years of strategic program or portfolio management leadership.
• Expertise in managing $25M+ technology investments with full budget and vendor oversight.
• Proven negotiator experienced in competitive bidding and contract development.
• Track record of building executive-grade AI dashboards for strategic decision-making.
• Advanced proficiency with AI tools for workflow optimization and insight generation.
• Exceptional problem-solving capabilities in high-stakes, ambiguous environments.
• Outstanding executive communication skills with proven C-suite influence.
• Based in the US, with willingness to travel 25% domestically and authorized to work without sponsorship.

Nice-to-have Requirements

• Experience in PMO establishment or transformation.
• Working knowledge of EdTech platforms and academic performance metrics.
• Background in technology-focused legal or procurement operations.

About 2 Hour Learning

2 Hour Learning is tearing down the outdated one-size-fits-all education model and replacing it with AI-driven, personalized learning. With top national performance and impressive growth metrics, 2 Hour Learning values talent and performance. Enjoy a dynamic, remote-friendly environment among innovators, educators, and AI specialists as we reprogram learning for the AI era.

Working with Us

This is a full-time (40 hours per week), long-term position available immediately. You will enter into an independent contractor agreement with Crossover as a Contractor of Record. Compensation is $200 USD per hour, equating to $400,000 USD per year based on a 40-hour week and 50 working weeks per year. Payment is made weekly. For more details, visit Crossover FAQs.

Key Skills/Competency

AI dashboards, vendor management, contract negotiation, strategic planning, program management, portfolio oversight, budget management, data analysis, EdTech, executive communication.