VP Portfolio Operations (Remote, 2 Hour Learning)

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 this at scale, dozens of initiatives, technology partners, contracts and investment decisions must move together. This VP Portfolio Operations role owns the operating outputs behind those decisions: dashboards, vendor scorecards, bid packages and contract controls. It is a full-time (40 hours per week), long-term remote position, open to contractors 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 approval.
• Use AI daily to analyze portfolio data, detect anomalies, surface underperformance, draft decision-ready outputs and reduce manual PMO administration.

Required profile

• Directly owned a portfolio of 10+ concurrent initiatives with at least $5M in budget responsibility, including authority over budget allocation, vendor selection or prioritization.
• Managed 5+ external technology vendors at once, such as SaaS providers, AI/ML platforms, marketing agencies or engineering firms.
• Built and maintained portfolio dashboards on delivery health, budget burn versus forecast, milestone completion and major risks.
• Can show a case where C-suite leaders used portfolio data to decide on a vendor renewal, budget reallocation or initiative deprioritization.
• Led competitive procurement, including bid evaluation, vendor scoring, negotiation and selection; authored or co-authored SOWs with measurable deliverables, milestones, SLAs and acceptance criteria.
• Negotiated commercial terms such as pricing, penalties, fee caps and exit clauses and enforced them through invoice validation or corrective action.
• Strong written communication, able to turn complex financial and operational data into concise recommendations, and able to analyze financial and vendor data quickly enough to recommend optimization, reallocation or vendor elimination.
• 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 position pays $100 USD per hour, about $200,000 USD per year at 40 hours per week and 50 weeks per year, paid weekly. Candidates enter into an independent contractor agreement with Crossover as Contractor of Record.