Director of Vendor Program Management (Remote)

About the role

2 Hour Learning is building an AI-powered education model that aims to give students a full day of academic progress in two hours. To run it at scale, dozens of initiatives, technology partners, contracts and investment decisions must move together. This Director of Vendor Program Management role owns the operating outputs behind those decisions: dashboards, vendor scorecards, competitive bid packages and contract controls. AI is part of the daily workflow, helping standardize updates, detect anomalies, compare bids, analyze vendor performance and validate invoices. The position is full-time (40 hours per week), remote, and requires an independent contractor agreement with Crossover as Contractor of Record.

Key responsibilities

• Build and maintain portfolio-level dashboards across 10+ concurrent initiatives, using AI to standardize updates, detect slippage and blockers, and give executives a trusted view of delivery, budget and risk.
• Run recurring vendor performance reviews and maintain rubric-based scorecards covering delivery, quality, cost, contractual commitments and qualitative 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.

Required profile

• Personally owned execution across 10+ concurrent initiatives with at least $5M in portfolio budget responsibility, tracking spend and recommending budget allocation, vendor selection and initiative priorities.
• Managed 5+ external technology vendors at once (e.g., SaaS providers, AI/ML platforms, marketing agencies, engineering firms).
• Built and maintained dashboards on delivery health, budget burn versus forecast, milestone completion and major risks.
• Pointed to a case where C-suite leaders used portfolio data to make a go/no-go decision on a vendor renewal, budget reallocation or initiative deprioritization.
• Led competitive procurement including bid evaluation, vendor scoring, negotiation and recommendations for executive approval.
• Authored or co-authored SOWs with measurable deliverables, milestone payments, SLAs and acceptance criteria; negotiated pricing, penalties, fee caps and exit clauses and enforced them through invoice validation.
• Strong written communication, able to turn complex financial and operational data into concise recommendations, and able to analyze financial and vendor-performance data quickly.
• Able to work US business hours.

Nice-to-have requirements

• Experience with AI-enabled dashboards, anomaly detection, predictive alerts or natural-language analysis in portfolio management.
• EdTech, technology, consulting or similar experience managing complex portfolios of external technology partners.
• Fluency with portfolio and delivery tools such as Linear or Jira.

The pay is $100 USD per hour, or $200,000 USD per year at 40 hours per week and 50 weeks per year, paid weekly.