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

You\'ve tracked milestones, built dashboards, flagged risks, and chased vendors. But your reports never moved decisions. You weren't the one calling the shots. 2 Hour Learning is developing an AI-powered education model that enables students to complete a full day of learning in two hours. Scaling that model demands the orchestration of dozens of initiatives, technology partners, contracts, and capital allocation decisions. Your role is to ensure the execution infrastructure is reliable enough for leadership to act decisively. You will control the operational artifacts that inform those decisions: portfolio dashboards that reveal delays before they escape, vendor scorecards anchored in contractual obligations, competitive bid frameworks that clarify trade-offs, and contract governance that blocks unapproved expenditure. AI will integrate into your workflow, enabling you to normalize updates, flag anomalies, evaluate bids, monitor vendor delivery, and audit invoices. This is not a traditional PMO role centered on meetings, process adherence, or polished status presentations. It is designed for an operator who expects their work to shape outcomes. When a vendor underdelivers, your data should make that undeniable. When spend diverges from contract terms, your controls should intercept it. When leadership faces a $5M decision, your outputs should enable them to commit with speed and clarity. If that degree of ownership aligns with what you\'ve been seeking, apply. What You Will Be Doing Maintain portfolio-level dashboards for 10+ parallel initiatives, leveraging AI to normalize status updates, identify delays, surface blockers, and deliver a reliable executive perspective on delivery, budget, and risk Conduct structured vendor performance reviews and maintain rubric-driven scorecards integrating delivery quality, cost efficiency, contractual adherence, and qualitative performance indicators Oversee competitive procurement for technology vendors, including the creation of structured bid packages, standardized comparisons, evaluation rubrics, SOW authorship, and evidence-supported recommendations Enforce contract and invoice governance by monitoring fee ceilings, milestone triggers, acceptance conditions, and amendments, then auditing invoices against signed agreements before authorizing payment Integrate AI into daily operations to parse portfolio data, detect outliers, highlight underperformance, generate decision-ready materials, and minimize manual administrative overhead What You Won\'t Be Doing Creating status reports that executives review but never reference when making decisions Operating a meeting-driven PMO where coordination supersedes tangible execution outcomes Managing vendor relationships as courtesy exercises while ignoring missed deliverables or commitments Delegating contracts, SOWs, invoices, or procurement decisions to others because they appear too commercial or technical Treating AI as an occasional convenience rather than a foundational component of your operating model Director Program Management Key Responsibilities Deliver dependable, AI-enhanced dashboards, scorecards, procurement frameworks, and contract controls that equip executives with the clarity and authority to hold vendors accountable, manage costs, and drive delivery across a $50M EdTech portfolio. Basic Requirements Owned a portfolio of 10+ concurrent initiatives with at least $5M in budget responsibility, including direct authority over budget allocation, vendor selection, or initiative prioritization Managed 5+ external technology vendors simultaneously, such as SaaS platforms, AI/ML providers, marketing agencies, or engineering firms Designed and maintained portfolio-level dashboards tracking metrics including delivery health, budget consumption versus forecast, milestone completion, and critical risks or blockers Can cite a specific instance where C-suite executives relied on your portfolio data to inform a go/no-go decision on vendor renewal, budget reallocation, or initiative deprioritization Led competitive technology procurement directly, including structured bid evaluation, vendor scoring, negotiation, and final selection Drafted or co-drafted SOWs incorporating measurable deliverables, milestone-based payments, SLAs, acceptance criteria, or other performance-linked terms Negotiated commercial provisions such as pricing structures, penalties, fee caps, or exit clauses, and enforced those provisions through invoice validation or corrective measures Possess strong written communication skills, with the ability to distill complex financial and operational data into concise, actionable recommendations for executives Can analyze financial and vendor-performance data with sufficient speed to recommend optimization, reallocation, or vendor termination Available to work US business hours Nice-to-have Requirements Experience applying AI-enabled dashboards, anomaly detection, predictive alerts, or natural-language analysis within portfolio management contexts Background in EdTech, technology, consulting, or similar environments managing complex portfolios of external technology partners Proficiency with portfolio and delivery tools such as Linear, Jira, or comparable systems 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. Working with us This is a full-time (40 hours per week), long-term position. The position is immediately available and requires entering into an independent contractor agreement with Crossover as a Contractor of Record. 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. The payment period is weekly. Consult for more details on this topic. #J-18808-Ljbffr Crossover