Director, AI-Powered Portfolio & Vendor Execution

Crossover; United States; Hybrid; USD 117,000 - 158,000; Full time

Job summary

Crossover is seeking an operator to own the execution layer behind critical decisions, building AI-powered dashboards and scorecards for a $50M EdTech portfolio. You’ll ensure spend adherence to contracts, validate invoices, and provide decision-ready outputs for executives.

This full-time contractor role requires managing multiple initiatives with $5M+ budgets, overseeing vendors, and delivering measurable impact through structured bid processes and SOWs. Works US business hours.

Qualifications

• Own portfolio of 10+ concurrent initiatives with at least $5M in budget responsibility, including authority over budget allocation, vendor selection, or initiative prioritization.
• Managed 5+ external technology vendors at the same time, such as SaaS providers, AI/ML platforms, marketing agencies, or engineering firms.
• Built and maintained portfolio-level dashboards covering metrics such as delivery health, budget burn versus forecast, milestone completion, and major risks or blockers.
• Can point to a case where C-suite leaders used your portfolio data to make a go/no-go decision on a vendor renewal, budget reallocation, or initiative deprioritization.
• Directly led competitive technology procurement, including structured bid evaluation, vendor scoring, negotiation, and selection.
• Authored or co-authored SOWs with measurable deliverables, milestone payments, SLAs, acceptance criteria, or other performance-based terms.
• Negotiated commercial terms such as pricing, penalties, fee caps, or exit clauses and enforced those terms through invoice validation or corrective action.
• Strong written communication skills, with the ability to turn complex financial and operational data into concise recommendations executives can act on.
• Able to analyze financial and vendor-performance data quickly enough to recommend optimization, reallocation, or vendor elimination.
• Able to work US business hours

Responsibilities

• Own portfolio-level dashboards across 10+ concurrent 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

Portfolio dashboards

Vendor management

SOW development

Contract controls

Invoice validation

AI dashboards

Data analysis

Executive communication

Vendor negotiation

Tools

Linear

Jira

Job description

Crossover is seeking an operator to own the execution layer behind critical decisions, building AI-powered dashboards and scorecards for a $50M EdTech portfolio. You’ll ensure spend adherence to contracts, validate invoices, and provide decision-ready outputs for executives.

This full-time contractor role requires managing multiple initiatives with $5M+ budgets, overseeing vendors, and delivering measurable impact through structured bid processes and SOWs. Works US business hours.