Program Management Officer, 2 Hour Learning
@ Trilogy

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

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Job Details

Overview

At 2 Hour Learning, you'll architect and operate an AI-powered control system for a $50M EdTech portfolio. This role is performance control and not traditional project management. You will drive vendor accountability and deliver academic impact through live dashboards, vendor scorecards, competitive bid evaluations, and enforceable contracts.

What You Will Be Doing

  • Owning a live, AI-powered execution dashboard for 25+ initiatives.
  • Building rubric-based vendor scorecards triggering actionable responses.
  • Running competitive vendor evaluations with clear scopes and budgets.
  • Negotiating enforceable contracts with defined performance criteria.
  • Writing memos that recommend decisive actions on vendor performance.

What You Won’t Be Doing

  • Coordinating passive templates.
  • Letting vendor issues bubble up.
  • Accepting ambiguous contracts or overdue milestones.
  • Writing reports without follow-up action.
  • Delegating core AI tasks to others.

Key Responsibilities

You will build and run the execution system that enforces vendor accountability, reallocates resources, and ensures high-quality on-time delivery.

Basic Requirements

  • 5+ years in Program/Portfolio Management or PMO leadership.
  • Experience managing $25M+ technology spend.
  • Track record in competitive bid processes and contract negotiations.
  • Experience with AI-powered dashboards and daily AI tool usage.
  • Strong executive communication and problem-solving skills.
  • U.S.-based, open to 25% domestic travel, eligible to work without sponsorship.

Nice-to-Have

  • Experience launching or overhauling a PMO or control system.
  • Familiarity with education tech platforms or academic metrics.
  • Exposure to legal, procurement, or contract governance in tech.

About 2 Hour Learning

2 Hour Learning is reprogramming education with an AI-driven, personalized approach that compresses a full school day into two hours without compromising outcomes.

Working with Us

This is a full-time, long-term role under an independent contractor agreement with Crossover. Compensation is $200 USD/hour ($400,000 USD/year) with weekly payments.

Key skills/competency

  • Program Management
  • Portfolio Management
  • AI Execution
  • Dashboard Management
  • Vendor Scorecards
  • Contract Negotiation
  • Bid Process
  • Performance Control
  • Executive Communication
  • EdTech
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How to Get Hired at Trilogy

🎯 Tips for Getting Hired

  • Customize your resume: Highlight program management with AI tools.
  • Demonstrate ownership: Showcase portfolio and vendor achievements.
  • Research Trilogy: Review mission, values, and recent news.
  • Prepare for interviews: Focus on vendor negotiations and dashboard metrics.

📝 Interview Preparation Advice

Technical Preparation

Review AI dashboard technologies.
Practice competitive bid process simulations.
Study contract negotiation techniques.
Familiarize with vendor scorecard methodologies.

Behavioral Questions

Explain your decision-making process.
Describe managing multi-million-dollar projects.
Discuss conflict resolution experiences.
Share vendor management success stories.

Frequently Asked Questions