AI-Powered Portfolio Execution Leader

Crossover; Cleveland (OH); Remote; USD 131,000 - 145,000; Full time

Job summary

Crossover is seeking a VP of Portfolio Operations to own AI-driven dashboards, vendor scorecards, and contract controls across a $50M EdTech portfolio. You will standardize updates, detect anomalies, and provide decision-ready outputs for executives while ensuring spend aligns with contracts.

This contractor role requires leading procurement, SOWs, and milestone-based payments, with a strong focus on measurable delivery and executive-level communication.

Qualifications

• Directly owned a portfolio of 10+ concurrent initiatives with budget responsibility.
• Managed 5+ external technology vendors simultaneously.
• Built dashboards covering delivery health, budgets, milestones and risks.
• Can show C-suite use of portfolio data for go/no-go decisions.
• Led competitive procurement with bid evaluation and vendor scoring.
• Authored SOWs with measurable deliverables and SLAs.
• Negotiated terms and enforced them via invoice validation.
• Translates complex data into concise exec recommendations.

Responsibilities

• Produce AI-powered dashboards, scorecards, procurement packages and contract controls for executives.
• Maintain trusted view of delivery, budget, and risk across 10+ initiatives.
• Run vendor performance reviews with rubric-based scoring.
• Develop structured bid packages and evidence-backed recommendations.
• Validate invoices against signed terms before spend approval.

Skills

Portfolio dashboards

Vendor scorecards

Competitive procurement

Contract controls

AI in portfolio management

Data analysis

Executive communication

Budget/financial acumen

Vendor performance tracking

Tools

Jira

Linear

Job description

Crossover is seeking a VP of Portfolio Operations to own AI-driven dashboards, vendor scorecards, and contract controls across a $50M EdTech portfolio. You will standardize updates, detect anomalies, and provide decision-ready outputs for executives while ensuring spend aligns with contracts.

This contractor role requires leading procurement, SOWs, and milestone-based payments, with a strong focus on measurable delivery and executive-level communication.