Director of Vendor Program Management, 2 Hour Learning (Remote) - $200,000/year USD

You've tracked progress. Built scorecards. Monitored vendors. Surfaced risks. But your analysis didn't drive the final decision. Someone else made the call. 2 Hour Learning is developing an AI-driven education model that enables students to complete a full day of learning in two hours. Scaling this model demands coordination across dozens of workstreams, technology partnerships, contracts, and capital allocation decisions. Your responsibility is to ensure the execution framework is reliable enough to support confident decision-making at the executive level.

About the role

You will deliver the operational intelligence that underpins executive decisions: portfolio dashboards that reveal delivery drift before it escalates, vendor performance scorecards anchored in contractual obligations, competitive procurement frameworks that clarify trade-offs, and contract governance that blocks unauthorized expenditure. AI will be integrated into your daily operations—standardizing status inputs, flagging irregularities, normalizing vendor bids, evaluating supplier performance, and cross-checking invoices.

This is not a traditional PMO position centered on status meetings, process adherence, or presentation polish. It is designed for an operator who expects their work to influence outcomes. When a vendor fails to deliver, your data should make that undeniable. When costs deviate from contract terms, your controls should surface it immediately. When leadership faces a $5M investment decision, your analysis should enable them to decide quickly and confidently.

Responsibilities

• Maintain portfolio-wide dashboards spanning 10+ parallel initiatives, leveraging AI to normalize status inputs, identify delays, highlight blockers, and ensure executives have a dependable view of delivery progress, financial status, and risk exposure
• Conduct structured vendor performance assessments and update rubric-driven scorecards that integrate delivery outcomes, quality metrics, cost efficiency, contractual adherence, and subjective performance indicators
• Direct competitive procurement for technology vendors, encompassing structured RFP packages, apples-to-apples bid analysis, evaluation frameworks, statement-of-work drafting, and evidence-supported selection recommendations
• Enforce contract and invoice discipline by monitoring rate caps, milestone triggers, acceptance conditions, and contract modifications, then verifying invoices against approved terms prior to payment authorization
• Embed AI into your daily workflow to examine portfolio trends, identify outliers, flag vendor underperformance, generate decision-ready summaries, and eliminate repetitive PMO tasks
• Deliver dependable, AI-enabled dashboards, performance scorecards, procurement frameworks, and contract oversight that equip executives with the visibility and leverage required to enforce vendor accountability, manage costs, and drive delivery across a $50M EdTech portfolio

What You Won’t Be Doing

• Creating status updates that executives review but do not rely on for decision-making
• Operating a meeting-centric PMO where process and coordination take precedence over tangible delivery outcomes
• Approaching vendor management as relationship stewardship while allowing missed commitments to go unaddressed
• Delegating contracts, statements of work, invoices, or procurement judgments to others because the content feels too commercial or too technical
• Treating AI as a sporadic productivity enhancement rather than a foundational component of your operating model

Requirements

• Held direct ownership of a portfolio comprising 10+ simultaneous initiatives with budget responsibility of at least $5M, including decision rights over budget distribution, vendor selection, or initiative prioritization
• Simultaneously managed 5+ external technology vendors, such as SaaS platforms, AI/ML solution providers, marketing firms, or software development contractors
• Developed and sustained portfolio-level dashboards tracking indicators like delivery health, budget consumption versus plan, milestone attainment, and critical risks or impediments
• Can cite a specific instance where executive leadership relied on your portfolio reporting to inform a go/no-go decision regarding vendor renewal, budget reallocation, or initiative suspension
• Led competitive technology vendor procurement end-to-end, including structured bid assessment, vendor evaluation, negotiation, and final selection
• Drafted or jointly drafted statements of work that included quantifiable deliverables, milestone-based payments, service-level agreements, acceptance criteria, or other performance-linked provisions
• Negotiated commercial contract terms including pricing structures, penalty clauses, fee ceilings, or termination provisions, and enforced compliance through invoice audits or corrective measures
• Demonstrated written communication capability, with the ability to distill complex financial and operational information into clear, actionable executive recommendations
• Capable of rapidly analyzing financial and vendor performance data to propose optimization strategies, budget reallocation, or vendor termination
• Available to work during US business hours

Nice-to-have Requirements

• Background using AI-powered dashboards, anomaly detection systems, predictive alerting, or natural-language data analysis in portfolio oversight
• Professional experience in EdTech, technology sectors, consulting, or similar fields involving complex portfolios of external technology partnerships
• Working knowledge of portfolio and project delivery platforms such as Linear, Jira, or comparable tools

About 2 Hour Learning

Education is broken, but 2 Hour Learning is proving it doesn’t have to be. They’re tearing down the outdated one-size-fits-all model and replacing it with AI-driven personalized learning that helps kids master academics in just two hours a day. With students consistently ranking in the top 1-2% nationally and the top 20% achieving an astonishing 6.5x growth, they’re proving that smarter learning is possible.

At 2 Hour Learning, it’s talent and performance that matter. They offer a dynamic, on-campus and remote-friendly environment where innovators, educators, and AI specialists can be a part of fixing a broken school system. 2 Hour Learning is reprogramming learning for the AI era.

Pay

The compensation level for this role is $100 USD/hour, which equates to $200,000 USD/year assuming 40 hours per week and 50 weeks per year.

Schedule

• Full-time (40 hours per week), long-term position
• Payment period is weekly
• Requires working during US business hours