Head of Program Management - 2 Hour Learning
@ Trilogy

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

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XXXXXXXXXX XXXXXXXXXXXXX XXXXXXXXXX******* @trilogy.com
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Job Details

Overview

Are you a seasoned program manager experienced with multi-million dollar portfolios and AI-driven tools? At Head of Program Management - 2 Hour Learning, you will design, oversee, and manage an AI-powered command center for a $50M EdTech portfolio.

What You Will Be Doing

  • Steer an AI-powered live dashboard for 25+ initiatives.
  • Create rubric-based vendor scorecards for decisive actions.
  • Conduct competitive vendor assessments and set budgets.
  • Negotiate clear, enforceable contracts with performance metrics.
  • Author memos on vendor performance and contract compliance.

What You Won't Be Doing

  • Simply coordinating; this role requires leadership.
  • Allowing vendor issues to go unresolved.
  • Tolerating vague contracts and missed deadlines.
  • Producing reports without actionable follow-up.
  • Delegating AI responsibilities entirely to others.

Basic Requirements

Minimum 5+ years in senior program management roles with ownership of $25M+ technology budgets. Proficient with AI-powered dashboards (e.g., Linear, Jira, Notion) and regular use of AI tools like GPT and Copilot. Proven ability to drive outcomes under high pressure with excellent executive communication skills. Must be US-based and willing to travel domestically up to 25%.

Nice-to-have

Experience in setting up or revamping a PMO, knowledge of education technology, or a background in legal/procurement within tech sectors.

About 2 Hour Learning

2 Hour Learning is revolutionizing education through AI-driven personalized learning, achieving outstanding student results by reprogramming traditional academic models.

Working with Us

This is a full-time, long-term role offered as an independent contractor position through Crossover. Compensation is $200 USD/hour, equating to $400,000 USD/year. Immediate availability required along with travel flexibility.

Key Skills/Competency

  • Program Management
  • AI Integration
  • Dashboard Design
  • Vendor Management
  • Contract Negotiation
  • Strategic Planning
  • Budget Management
  • EdTech Knowledge
  • Executive Communication
  • Risk Management
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How to Get Hired at Trilogy

🎯 Tips for Getting Hired

  • Research Trilogy's culture: Study their mission, values, and recent projects.
  • Customize your resume: Highlight AI and EdTech experience.
  • Emphasize leadership: Demonstrate portfolio and vendor management.
  • Prepare for tough interviews: Practice contract negotiation scenarios.

📝 Interview Preparation Advice

Technical Preparation

Familiarize with AI dashboard tools
Review vendor scorecard creation methods
Practice contract drafting techniques
Study competitive vendor assessment cases

Behavioral Questions

Describe a time you solved vendor disputes
Explain decision-making under pressure
Demonstrate leadership in ambiguous situations
Discuss managing large-scale projects

Frequently Asked Questions