Head of Program Management - 2 Hour Learning @ Trilogy
Your Application Journey
Email Hiring Manager
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
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.