Job Title: Director of Program Operations
Company: 2 Hour Learning, which is building an AI-powered education model designed to help students achieve a full day of academic progress in two hours
Job Type: Not specified
Location: Remote
Salary/Pay: $200,000 per year USD
Experience: Senior level. Has directly owned a portfolio of 10+ concurrent initiatives with at least $5M in budget responsibility, and has managed 5+ external technology vendors at the same time.
Skills Required:
- Portfolio management: building and maintaining portfolio-level dashboards covering delivery health, budget burn versus forecast, milestones, and risks
- Procurement: leading competitive technology procurement, including bid evaluation, vendor scoring, negotiation, and selection
- Contracts: authoring or co-authoring SOWs with measurable deliverables, milestone payments, SLAs, or acceptance criteria
- Commercial negotiation: negotiating pricing, penalties, fee caps, or exit clauses, and enforcing them through invoice validation or corrective action
- Executive decision support: a track record of C-suite leaders using your portfolio data to make go/no-go decisions on vendor renewals, budget reallocation, or initiative deprioritization
- Analysis: analyzing financial and vendor-performance data quickly to recommend optimization, reallocation, or vendor elimination
- Communication: strong written communication, turning complex financial and operational data into concise recommendations
- Availability: able to work US business hours
Advantage: Experience using AI-enabled dashboards, anomaly detection, predictive alerts, or natural-language analysis in portfolio management; experience in EdTech, technology, consulting, or another environment managing complex portfolios of external technology partners; fluency with portfolio and delivery tools such as Linear, Jira, or similar
Date Posted: Oct 27, 2026
Application Deadline: Not specified
Description:
Crossover is hiring a Director of Program Operations for 2 Hour Learning to make the execution layer of a $50M EdTech portfolio trustworthy enough for executives to act on. The role is not a meeting-heavy PMO position: it is for an operator whose work has consequences, using AI daily to analyze portfolio data, detect anomalies, and draft decision-ready outputs. Your work will include:
- Owning portfolio-level dashboards across 10+ concurrent initiatives, using AI to standardize updates, detect slippage, expose blockers, and maintain an executive view of delivery, budget, and risk
- Running recurring vendor performance reviews and maintaining rubric-based scorecards that combine delivery, quality, cost, contractual commitments, and qualitative signals
- Leading competitive technology-vendor procurement, including structured bid packages, normalized comparisons, scoring rubrics, SOW development, and evidence-backed recommendations
- Governing contracts and invoices by tracking fee caps, milestones, acceptance criteria, and amendments, and validating invoices against signed terms before spend is approved
- Using AI daily to surface underperformance and reduce manual PMO administration
How to Apply: Apply here.