Head of Program Management - 2 Hour Learning
@ Trilogy

Hybrid
$400,000
Hybrid
Full Time
Posted 22 days ago

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XXXXXXXXX XXXXXXXXXXX XXXXXXXXX****** @trilogy.com
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Job Details

About the Role

The Head of Program Management - 2 Hour Learning at Trilogy is seeking a seasoned program manager to lead a $50M EdTech portfolio with an AI-powered approach. This role emphasizes autonomy, performance control, and rapid execution with a focus on actionable insights over passive management.

What You Will Be Doing

  • Steer an AI-powered live dashboard for 25+ initiatives.
  • Create rubric-based vendor scorecards to initiate decisive actions.
  • Conduct competitive vendor assessments with clear scopes and budgets.
  • Negotiate enforceable contracts ensuring performance alignment.
  • Author memos on vendor performance and contract breaches.

What You Won’t Be Doing

  • Simply coordinating tasks or using templates.
  • Allowing issues to simmer without escalation.
  • Tolerating vague contracts or missed deadlines.
  • Producing reports without actionable follow-up.
  • Delegating core AI tasks externally.

Key Responsibilities

Design and manage an execution framework that ensures vendor accountability and timely, quality delivery. Oversee resource allocation and performance across a $50M portfolio.

Basic Requirements

  • 5+ years in senior Program/Portfolio/PMO leadership.
  • Ownership of $25M+ technology budgets.
  • Experience in competitive bidding and robust contract drafting.
  • Proficiency in AI-powered dashboards (e.g., Linear, Jira, Notion).
  • Regular usage of AI tools for task automation and insights.
  • Strong executive communication influencing C-suite decisions.
  • US-based with willingness to travel domestically up to 25%.

Nice-to-have Requirements

  • Experience with PMO setup or revamp.
  • Knowledge in education technology or academic performance metrics.
  • Background in legal, procurement, or contract management.

About 2 Hour Learning

2 Hour Learning is revolutionizing education by condensing a full school day's learning into two hours using cutting-edge AI. With impressive student performance metrics, they focus on talent and performance, offering a remote-friendly and dynamic environment.

Working with Us

This full-time position (40 hours per week) is immediately available under an independent contractor agreement with Crossover as a Contractor of Record. Compensation is $200 USD/hour, equating to $400,000 USD/year based on a 40-hour week over 50 weeks, with weekly payments.

Key skills/competency

  • Program Management
  • Portfolio Management
  • AI Integration
  • Vendor Management
  • Contract Negotiation
  • Dashboard Analytics
  • Project Leadership
  • Budget Management
  • EdTech
  • Strategic Communication
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How to Get Hired at Trilogy

🎯 Tips for Getting Hired

  • Customize your resume: Highlight AI and vendor management experience.
  • Research Trilogy: Understand their mission and EdTech focus.
  • Emphasize leadership: Showcase strategic decision-making in portfolios.
  • Review contract skills: Demonstrate negotiation and financial control.

📝 Interview Preparation Advice

Technical Preparation

Review AI dashboard tools usage.
Practice vendor contract case studies.
Study budgeting for large-scale projects.
Sharpen competitive bidding process knowledge.

Behavioral Questions

Describe a time you led a high-pressure team.
Explain your decision-making approach under uncertainty.
Share an example of rapid project pivoting.
Discuss a conflict resolution with vendors.

Frequently Asked Questions