Director, AI-Driven Portfolio Operations

Alpha School; United States; Hybrid; USD 114,000 - 162,000; Full time

Job summary

2 Hour Learning is seeking a Director of Program Operations to own the execution layer behind strategic procurement and portfolio governance. You will build AI-powered dashboards and scorecards that expose slippage, manage vendor performance, and govern contracts and invoices to prevent overspend.

This is a senior operator role with real impact on $50M+ EdTech initiatives. You will lead structured bid packages, SOWs, and evidence-backed recommendations, ensuring executives have decision-ready

Qualifications

• Directly owned a portfolio of 10+ concurrent initiatives with substantial budget responsibility.
• Managed multiple external technology vendors simultaneously (SaaS, AI/ML, agencies).
• Built portfolio dashboards showing delivery health, budget versus forecast, milestones and risks.
• Able to cite cases where execs used portfolio data to make go/no-go decisions.
• Led competitive procurement, including bid evaluation and vendor scoring.
• Authored or co-authored SOWs with measurable deliverables and payment terms.

Responsibilities

• Own portfolio-level dashboards across 10+ initiatives, using AI to standardize updates, detect slippage, expose blockers, and maintain a trusted executive view of delivery, budget, and risk
• Run recurring vendor performance reviews and maintain rubric-based scorecards that combine delivery, quality, cost, contractual commitments, and qualitative performance 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 spend is approved
• Use AI daily to analyze portfolio data, detect anomalies, surface underperformance, draft decision-ready outputs, and reduce manual PMO administration

Skills

Vendor management

Budget management

Executive communication

Data analysis

Problem solving

Tools

Linear

Jira

Job description

2 Hour Learning is seeking a Director of Program Operations to own the execution layer behind strategic procurement and portfolio governance. You will build AI-powered dashboards and scorecards that expose slippage, manage vendor performance, and govern contracts and invoices to prevent overspend.

This is a senior operator role with real impact on $50M+ EdTech initiatives. You will lead structured bid packages, SOWs, and evidence-backed recommendations, ensuring executives have decision-ready