Director of AI-Powered Program Management & Delivery

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

Benefits offered by this job

Contractor of Record

Job summary

2 Hour Learning is building an AI‑powered education model to help students achieve a full day of progress in just two hours. As Director of Program Management, you will own portfolio dashboards, vendor scorecards, and contract controls to give executives clear, data-driven visibility and the ability to act decisively on spend and delivery.

This full-time, contractor-of-record role with Crossover offers weekly pay, $100/hour, and a remote-friendly environment.

Qualifications

• Directly owned a portfolio of 10+ initiatives with budget responsibility.
• Built and maintained dashboards showing delivery health, budget burn vs forecast, and risks.
• Led competitive procurement with structured bid packages and evidence-backed recommendations.
• Authored SOWs with measurable deliverables and milestones.
• Negotiated terms and enforced them via invoice validation.

Responsibilities

• Produce AI-powered dashboards and scorecards for executives.
• Run vendor performance reviews with rubric-based scoring.
• Lead competitive procurement and bid evaluation.
• Govern contracts and validate invoices against terms.

Skills

Dashboard management

Vendor management

Procurement

SOW development

Budget oversight

Contract governance

AI in PMO

Tools

Jira

Linear

Job description

2 Hour Learning is building an AI‑powered education model to help students achieve a full day of progress in just two hours. As Director of Program Management, you will own portfolio dashboards, vendor scorecards, and contract controls to give executives clear, data-driven visibility and the ability to act decisively on spend and delivery.

This full-time, contractor-of-record role with Crossover offers weekly pay, $100/hour, and a remote-friendly environment.