Program Director, 2 Hour Learning
@ Trilogy

Hybrid
$400,000
Hybrid
Full Time
Posted 8 hours ago

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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performance and significant growth in student outcomes, the focus is on talent and robust performance rather than outdated methods.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.

📝 Interview Preparation Advice

Technical Preparation

Review AI execution dashboards.
Practice data analytics tools.
Familiarize with Linear, Jira, Notion.
Study contract management systems.

Behavioral Questions

Describe a time you led vendor negotiations.
Explain resolving high-stakes project issues.
Share experience driving strategic initiatives.
Discuss adapting in ambiguous situations.

Frequently Asked Questions