Program Director, 2 Hour Learning
@ Trilogy

Hybrid
$400,000
Hybrid
Full Time
Posted 2 days ago

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Job Details

About the Role

At 2 Hour Learning, a visionary initiative under Trilogy, the Program Director is the architect behind revolutionizing education. The role requires transforming a $50M EdTech portfolio into a performance-driven machine using AI-enhanced dashboards and data-driven contract strategies.

Key Responsibilities

  • Architect an AI-enhanced command center for real-time insights.
  • Design and implement vendor evaluation systems based on data.
  • Spearhead vendor selection through competitive evaluations.
  • Craft contracts aligning vendor incentives with educational outcomes.
  • Author action memos translating performance data into decisions.

What You Won’t Be Doing

  • Assuming a passive coordinator role.
  • Watching issues escalate without decisive action.
  • Accepting mediocrity in contracts or financial management.
  • Creating reports that do not drive immediate action.
  • Outsourcing AI expertise – hands-on involvement is expected.

Basic Requirements

  • 5+ years in strategic program or portfolio management leadership.
  • Experience managing $25M+ technology investments with full oversight.
  • Expert negotiator with competitive bidding and contract experience.
  • Proven track record building executive-grade AI dashboards.
  • Advanced proficiency in AI tools for optimizing workflows.
  • Outstanding problem-solving skills in ambiguous, high-stakes environments.
  • Exceptional executive communication with C-suite influence.
  • US-based with 25% domestic travel and work authorization.

Nice-to-have Requirements

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

About 2 Hour Learning

2 Hour Learning is reprogramming education with AI-driven personalized learning. They aim to compress a full school day into two hours of focused, effective learning, challenging the outdated education model. The environment is dynamic, with a blend of remote and on-campus settings where educators, innovators, and AI experts collaborate to fix a broken school system.

Working with Us

This is a full-time, long-term independent contractor role through Crossover. Compensation is $200 USD per hour, equating to $400,000 USD per year, with weekly payments. Immediate start with detailed process available at Crossover.

Key Skills/Competency

  • AI
  • Portfolio Management
  • Vendor Management
  • Contract Negotiation
  • Dashboard Development
  • Data Analysis
  • Strategic Planning
  • Education
  • EdTech
  • Leadership
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How to Get Hired at Trilogy

🎯 Tips for Getting Hired

  • Customize your resume: Highlight portfolio and AI experience.
  • Research Trilogy: Understand the company’s mission and innovation.
  • Show concrete results: Emphasize measurable achievements.
  • Prepare for data questions: Practice vendor management and AI discussions.

📝 Interview Preparation Advice

Technical Preparation

Review AI dashboard development basics.
Study vendor evaluation methodologies.
Practice data analysis using real datasets.
Familiarize with contract negotiation tools.

Behavioral Questions

Describe strategic decision-making under pressure.
Explain how you managed large-scale portfolios.
Share negotiation experiences with tough vendors.
Discuss leadership in ambiguous environments.

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