Director Program Management, 2 Hour Learning (Remote)

You have experience building dashboards, tracking milestones, managing vendors, and identifying risks, but now you want your work to directly influence critical decisions. At 2 Hour Learning, an AI-driven education company revolutionizing how students achieve academic progress, we are seeking a Director of Program Management to lead the execution layer that drives strategic decisions. This role involves managing a complex portfolio of initiatives, technology partners, contracts, and investments to ensure seamless alignment and trustworthy operational insights for executives.

As the Director of Program Management, you will be responsible for creating and maintaining portfolio dashboards that highlight potential delays before they become issues, vendor scorecards linked to contractual commitments, competitive bid packages that clarify trade-offs, and contract controls that prevent unauthorized spending. AI tools will be integral to your daily workflow, helping you standardize updates, detect anomalies, compare bids, evaluate vendor performance, and validate invoices. This position is for a hands-on operator who values measurable impact over routine reporting or meeting-heavy coordination.

Key Responsibilities
- Own and maintain portfolio-level dashboards across 10+ concurrent initiatives, leveraging AI to standardize updates, detect slippage, expose blockers, and provide executives with a trusted view of delivery, budget, and risk.
- Conduct recurring vendor performance reviews using rubric-based scorecards that assess delivery, quality, cost, contractual commitments, and qualitative factors.
- Lead competitive technology-vendor procurement processes, 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, ensuring invoices align with signed terms before approving spend.
- Utilize AI daily to analyze portfolio data, identify anomalies, highlight underperformance, generate decision-ready outputs, and reduce manual administrative tasks.

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-level 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 go/no-go decisions on vendor renewals, budget reallocations, or initiative prioritization.
- Led competitive technology procurement involving structured 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 action.
- Strong written communication skills with the ability to translate complex financial and operational data into concise, actionable executive recommendations.
- Skilled at quickly analyzing financial and vendor performance data to recommend optimization, reallocation, or vendor elimination.
- Availability to work during 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 transforming education by replacing outdated models with AI-driven personalized learning that enables students to master academics in just two hours a day. Students consistently rank in the top 1-2% nationally, with the top 20% achieving remarkable growth. The company offers a dynamic, hybrid work environment where innovators, educators, and AI specialists collaborate to fix a broken school system.

This is a full-time, long-term position requiring an independent contractor agreement. Compensation is $100 USD per hour, equating to approximately $200,000 USD annually based on a 40-hour workweek and 50 working weeks per year. Weekly payments are made. If you are ready to take ownership and make a measurable impact in a fast-paced, AI-driven environment, we encourage you to apply.