Director of Vendor Programs & AI-Driven Execution

Crossover; Cleveland (OH); Hybrid; USD 114,000 - 162,000; Full time

Job summary

2 Hour Learning is seeking an operator to own portfolio dashboards, vendor scorecards, and contract controls for a multi-million EdTech portfolio. You’ll enable executives to act with confidence by surfacing slippage, performance gaps, and spend deviations using AI-powered insights.

The role emphasizes concrete execution over meetings, delivering decision-ready outputs and enforceable controls. This is a full-time contractor role with immediate impact.

Qualifications

• Directly owned a portfolio of 10+ initiatives with budget responsibility
• Managed 5+ external technology vendors concurrently
• Built portfolio dashboards covering delivery health, budget burn, milestones, and risks

Responsibilities

• Produce reliable, AI-powered dashboards and scorecards for executives
• Maintain rubric-based vendor performance reviews and SOW development
• Lead competitive technology procurement with structured bid packages and evidence-backed recommendations
• Govern contracts and invoices by tracking fee caps, milestones, acceptance criteria, and amendments
• Validate invoices against signed terms before spend is approved

Skills

Portfolio management

Vendor management

SOW development

Budget oversight

Contract negotiation

Data-driven decision making

AI dashboards familiarity

Tools

Linear

Jira

Job description

2 Hour Learning is seeking an operator to own portfolio dashboards, vendor scorecards, and contract controls for a multi-million EdTech portfolio. You’ll enable executives to act with confidence by surfacing slippage, performance gaps, and spend deviations using AI-powered insights.

The role emphasizes concrete execution over meetings, delivering decision-ready outputs and enforceable controls. This is a full-time contractor role with immediate impact.