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

You've tracked milestones, flagged risks, and chased down vendors. You've built dashboards and written reports. But when it came time to decide, someone else made the call. 2 Hour Learning is developing an AI-powered education model that enables students to accomplish a full day of learning in two hours. Scaling that model depends on coordinating dozens of initiatives, technology partnerships, contracts, and capital decisions. Your role is to ensure the execution infrastructure is reliable enough to support executive decision-making with confidence. You will control the operational outputs that inform those decisions: portfolio dashboards that reveal delays before they escalate, vendor scorecards anchored to contractual obligations, competitive procurement packages that clarify trade-offs, and contract governance that blocks unauthorized spend. AI will integrate into your daily operations—standardizing status updates, identifying outliers, evaluating bids, assessing vendor results, and verifying invoices. This is not a PMO function centered on meeting cadences, compliance rituals, or presentation refinement. It is designed for someone who expects their work to drive outcomes. If a vendor falls short, your documentation should make it undeniable. If costs drift beyond agreed terms, your controls should stop it. When leadership weighs a $5M commitment, your analysis should enable rapid, informed action.

About the role

Deliver dependable, AI-enhanced dashboards, scorecards, procurement structures, and contract oversight that equip executives with the transparency and control needed to enforce vendor accountability, manage costs, and drive execution across a $50M EdTech portfolio.

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 that integrate delivery results, cost performance, quality metrics, contractual adherence, and subjective observations
• Manage competitive procurement for technology vendors, including the creation of 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

What You Won’t Be Doing

• Creating status updates that executives acknowledge but do not reference when making decisions
• Operating a coordination-focused PMO where meetings consume more energy than measurable progress
• Viewing vendor management as relationship upkeep while contractual shortfalls are left unaddressed
• Handing off contracts, SOWs, invoices, or procurement decisions because they appear too technical or commercial to own
• Treating AI as a sporadic productivity enhancement rather than a fundamental component of your workflow

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. 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

This is a full-time (40 hours per week), long-term position. The payment period is weekly.