Director, AI-Driven Portfolio Delivery

Crossover; Atlanta (GA); Hybrid; USD 180,000 - 210,000; Full time

Job summary

2 Hour Learning seeks an operator-level Director of Program Management to own the execution layer across a multi-initiative portfolio. You will deliver AI-powered dashboards and evidence-backed vendor scorecards that expose slippage, guide procurement, and enforce contract terms.

The role emphasizes actionable outputs over meetings and status decks. You will manage 10+ concurrent initiatives with significant budgets, lead vendor engagements, and ensure executive confidence to act on

Qualifications

• Portfolio of 10+ initiatives with $5M+ budget.
• Managed 5+ external technology vendors.
• Built portfolio dashboards covering delivery, budget, risks.
• C-suite used portfolio data for go/no-go decisions.
• Led competitive technology procurement and scoring.
• Authored measurable SOWs and SLAs.
• Negotiated terms including penalties and fee caps.
• Strong written communication translating data for execs.
• Able to analyze financial/vendor data quickly for optimization.
• Must work US business hours.

Responsibilities

• Own portfolio-level dashboards across 10+ initiatives with AI-driven updates.
• Run vendor performance reviews with rubric-based scorecards.
• Lead competitive procurement including bids, scoring, and SOWs.
• Govern contracts and invoices; validate against signed terms.
• Use AI to analyze portfolio data and produce decision-ready outputs.

Skills

Portfolio ownership

Vendor management

Dashboarding

Contract negotiations

SOW development

Data analysis

Executive communication

AI integration

US business hours

Tools

Linear

Jira

Job description

2 Hour Learning seeks an operator-level Director of Program Management to own the execution layer across a multi-initiative portfolio. You will deliver AI-powered dashboards and evidence-backed vendor scorecards that expose slippage, guide procurement, and enforce contract terms.

The role emphasizes actionable outputs over meetings and status decks. You will manage 10+ concurrent initiatives with significant budgets, lead vendor engagements, and ensure executive confidence to act on