Director Program Management (AI Education Portfolio)

About the role

2 Hour Learning is building an AI-powered education model that aims to give students a full day of academic progress in two hours. As Director of Program Management you will own the operating outputs behind the decisions made by executives: portfolio dashboards, vendor scorecards, competitive bid packages and contract controls. The role is remote, full-time (40 hours per week) and long-term, and requires entering into an independent contractor agreement with Crossover as Contractor of Record.

Key responsibilities

• Build and run portfolio-level dashboards across 10+ concurrent initiatives, using AI to standardize updates, detect slippage and blockers, and keep a trusted executive view of delivery, budget and risk.
• Run recurring vendor performance reviews and maintain rubric-based scorecards covering delivery, quality, cost, contractual commitments and qualitative signals.
• Lead competitive technology-vendor procurement, including structured bid packages, normalized comparisons, scoring rubrics, SOW development and evidence-backed recommendations.
• Govern contracts and invoices by tracking fee caps, milestones, acceptance criteria and amendments, then validating invoices against signed terms before approval.
• Use AI daily to analyze portfolio data, detect anomalies, surface underperformance, draft decision-ready outputs and reduce manual PMO administration.

Required profile

• Directly owned 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 at once, such as SaaS providers, AI/ML platforms, marketing agencies or engineering firms.
• Built and maintained portfolio dashboards on delivery health, budget burn versus forecast, milestone completion and major risks.
• Can show a case where C-suite leaders used your portfolio data to make a go/no-go decision on a vendor renewal, budget reallocation or initiative deprioritization.
• Led competitive technology procurement, including bid evaluation, vendor scoring, negotiation and selection.
• Authored or co-authored SOWs with measurable deliverables, milestone payments, SLAs and acceptance criteria.
• Negotiated commercial terms such as pricing, penalties, fee caps and exit clauses and enforced them through invoice validation or corrective action.
• Strong written communication, able to turn complex financial and operational data into concise recommendations; able to analyze financial and vendor-performance data quickly.
• Able to work US business hours.

Nice-to-have requirements

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

The pay is $100 USD per hour, or $200,000 USD per year at 40 hours per week and 50 weeks per year, paid weekly.