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

About the Role

You will ensure the execution infrastructure is reliable enough to support executive decision-making with confidence. Your role is to control the operational outputs that inform those decisions: portfolio dashboards revealing delays before they escalate, vendor scorecards anchored to contractual obligations, competitive procurement packages clarifying trade-offs, and contract governance blocking unauthorized spend. AI will integrate into your daily operations—standardizing status updates, identifying outliers, evaluating bids, assessing vendor results, and verifying invoices. This is designed for someone who expects their work to drive outcomes.

Responsibilities

• Maintain portfolio-level dashboards for 10+ parallel initiatives, leveraging AI to normalize status inputs, identify delays, flag obstacles, and sustain an executive-ready view of progress, spend, and exposure.
• Conduct scheduled vendor performance evaluations and maintain structured scorecards integrating delivery results, cost performance, quality metrics, contractual adherence, and subjective observations.
• Manage competitive procurement for technology vendors, including structured bid requests, normalized vendor comparisons, evaluation frameworks, SOW drafting, and data-driven selection recommendations.
• Enforce contract and invoice discipline by monitoring rate caps, milestone triggers, acceptance standards, and contract modifications—then cross-checking invoices against approved terms before authorizing payment.
• Apply AI tools daily to interpret portfolio metrics, flag deviations, highlight vendor gaps, generate decision-ready summaries, and minimize repetitive administrative overhead.
• Deliver dependable, AI-enhanced dashboards, scorecards, procurement structures, and contract oversight that equip executives with transparency and control to enforce vendor accountability, manage costs, and drive execution across a $50M EdTech portfolio.

Requirements

• Previously owned a portfolio of 10+ simultaneous initiatives with at least $5M in budget oversight, including decision rights over budget deployment, vendor selection, or initiative ranking.
• Simultaneously managed 5+ external technology vendors, such as SaaS platforms, AI/ML providers, marketing agencies, or development firms.
• Created and maintained portfolio-level dashboards tracking metrics including delivery status, budget consumption versus plan, milestone attainment, and critical risks or impediments.
• Can identify an instance where C-level executives relied on your portfolio reporting to decide whether to renew a vendor, reallocate budget, or deprioritize an initiative.
• Led competitive technology procurement directly, including the design of structured evaluation processes, vendor scoring, negotiation, and final selection.
• Drafted or co-drafted SOWs containing measurable outputs, milestone-based payment schedules, SLAs, acceptance criteria, or other performance-linked provisions.
• Negotiated commercial elements such as pricing structures, penalty terms, fee limits, or termination rights and enforced those provisions via invoice review or corrective measures.
• Possesses strong written communication abilities, capable of distilling complex operational and financial information into clear, actionable executive recommendations.
• Can rapidly analyze financial and vendor performance data to propose optimization strategies, budget shifts, or vendor termination.
• Available to work US business hours.

Nice-to-have Requirements

• Prior use of AI-powered dashboards, anomaly detection, predictive alerting, or natural-language processing in portfolio oversight.
• Background in EdTech, technology sectors, consulting, or other settings requiring management of multifaceted external technology partnerships.
• Proficiency with 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.

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

This is a full-time (40 hours per week), long-term position with weekly payments.