Principal Program Manager, 2 Hour Learning (Remote)

You will play a critical role in driving execution for 2 Hour Learning’s AI-powered education platform, designed to help students achieve a full day of academic progress in just two hours. This position requires managing a complex portfolio of initiatives, technology partners, contracts, and investments to ensure seamless alignment and trustworthy operational outputs. Your work will provide executives with clear, actionable insights through portfolio dashboards, vendor scorecards, competitive bid packages, and contract controls—all powered by AI to enhance accuracy and efficiency. This role is for a hands-on operator who values measurable impact and accountability, not just process compliance or status reporting.

Key Responsibilities

- Own and maintain portfolio-level dashboards across 10+ concurrent initiatives, leveraging AI to standardize updates, detect slippage, identify blockers, and provide executives with a reliable view of delivery, budget, and risk.
- Conduct recurring vendor performance reviews using rubric-based scorecards that evaluate delivery, quality, cost, contractual commitments, and qualitative performance indicators.
- Lead competitive procurement processes for technology vendors, including preparing structured bid packages, normalizing comparisons, developing scoring rubrics, drafting Statements of Work (SOWs), and delivering evidence-backed recommendations.
- Govern contracts and invoices by monitoring fee caps, milestones, acceptance criteria, and amendments; validate invoices against signed terms before approving spend.
- Utilize AI daily to analyze portfolio data, detect anomalies, highlight underperformance, draft decision-ready reports, and reduce manual project management administration.

Required Qualifications

- Proven experience managing a portfolio of 10+ concurrent initiatives with at least $5M in budget responsibility, including authority over budget allocation, vendor selection, or initiative prioritization.
- Managed 5+ external technology vendors simultaneously, such as SaaS providers, AI/ML platforms, marketing agencies, or engineering firms.
- Developed and maintained portfolio dashboards tracking delivery health, budget burn versus forecast, milestone completion, and major risks or blockers.
- Demonstrated impact where C-suite leaders used your portfolio data to make critical decisions on vendor renewals, budget reallocations, or initiative prioritization.
- Led competitive technology procurement processes, including bid evaluation, vendor scoring, negotiation, and selection.
- Authored or co-authored SOWs with measurable deliverables, milestone payments, SLAs, acceptance criteria, or other performance-based terms.
- Negotiated commercial terms such as pricing, penalties, fee caps, or exit clauses, and enforced these through invoice validation or corrective actions.
- Strong written communication skills with the ability to translate complex financial and operational data into concise, actionable executive recommendations.
- Ability to analyze financial and vendor performance data quickly to recommend optimization, reallocation, or vendor elimination.
- Availability to work US business hours.

Preferred Qualifications and Benefits

- Experience using AI-enabled dashboards, anomaly detection, predictive alerts, or natural-language analysis in portfolio management.
- Background in EdTech, technology, consulting, or managing complex portfolios of external technology partners.
- Familiarity with portfolio and delivery tools such as Linear, Jira, or similar systems.

2 Hour Learning is revolutionizing education by replacing traditional one-size-fits-all models with AI-driven personalized learning that enables students to master academics efficiently. Their students consistently rank in the top 1-2% nationally, with the top 20% achieving up to 6.5 times growth. The company fosters a dynamic, hybrid work environment where innovators, educators, and AI specialists collaborate to transform a broken school system.

This is a full-time, long-term independent contractor role with a competitive compensation rate equivalent to $200,000 USD annually, based on a 40-hour workweek. The position offers the opportunity to make a significant impact in a fast-growing EdTech company focused on AI-powered learning solutions.