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

About the Role

2 Hour Learning is developing an AI-driven education platform designed to enable students to accomplish a complete day of learning in two hours. Delivering this platform at scale demands coordination across numerous initiatives, technology partnerships, contractual agreements, and capital allocation decisions. Your role is to ensure the execution infrastructure is dependable enough to support executive decision-making. You will be accountable for the operational outputs that inform those decisions: portfolio dashboards, vendor scorecards, structured bid evaluations, and contract governance.

This is not a traditional PMO position centered on meetings or procedural adherence. It is designed for an operator who seeks consequential impact, where your analysis and oversight directly influence executive decisions on vendor accountability, expenditure, and execution velocity across a $50M EdTech portfolio.

Responsibilities

• Manage portfolio-level dashboards covering 10+ simultaneous initiatives, leveraging AI to normalize status inputs, identify delays, highlight obstacles, and sustain an accurate executive perspective on delivery progress, financial status, and exposure.
• Conduct scheduled vendor performance assessments and maintain structured scorecards that integrate delivery outcomes, quality metrics, cost performance, contractual adherence, and subjective evaluation factors.
• Oversee competitive procurement processes for technology vendors, including creation of standardized bid requests, side-by-side comparisons, evaluation frameworks, statement of work drafting, and data-supported selection recommendations.
• Administer contract and invoice oversight by monitoring rate limits, milestone conditions, acceptance standards, and contract modifications, then confirming invoice accuracy against executed agreements prior to payment authorization.
• Apply AI tools on a daily basis to examine portfolio information, flag outliers, identify performance gaps, generate decision-ready materials, and minimize repetitive administrative tasks.
• Deliver dependable, AI-enabled dashboards, scorecards, procurement materials, and contractual oversight that equip executives with the transparency and control necessary to enforce vendor accountability, manage expenditure, and drive execution velocity.

What You Won’t Be Doing

• Creating status updates that executives review but do not rely on for making decisions.
• Operating a meeting-intensive PMO where process coordination takes precedence over tangible execution outcomes.
• Approaching vendor management as relationship stewardship while allowing missed obligations to remain unaddressed.
• Delegating contracts, statements of work, invoices, or procurement activities to others because they appear overly commercial or technical in nature.
• Treating AI as an infrequent productivity enhancement rather than a fundamental component of your operations.

Requirements

• Previously owned a portfolio consisting of 10+ simultaneous initiatives with a minimum of $5M in budgetary accountability, including decision-making authority over budget distribution, vendor appointment, or initiative ranking.
• Simultaneously managed 5+ external technology vendors, including SaaS providers, AI/ML platforms, marketing agencies, or engineering firms.
• Developed and sustained portfolio-level dashboards that tracked indicators such as delivery status, budget consumption relative to projections, milestone achievement, and critical risks or impediments.
• Can reference a specific instance where executive leadership relied on your portfolio reporting to inform a go/no-go decision regarding vendor contract renewal, budget reallocation, or initiative deprioritization.
• Personally led competitive technology procurement processes, encompassing structured bid assessment, vendor evaluation, negotiation, and final selection.
• Drafted or jointly drafted SOWs that included quantifiable deliverables, milestone-based payments, SLAs, acceptance criteria, or other performance-linked provisions.
• Negotiated commercial provisions including pricing structures, penalties, fee ceilings, or termination rights, and enforced these provisions via invoice review or remediation actions.
• Excellent written communication capabilities, with proficiency in converting intricate financial and operational information into brief, actionable recommendations for executive consumption.
• Capable of rapidly analyzing financial and vendor performance data to propose optimization strategies, budget realignment, 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 analysis within portfolio management contexts.
• Experience in EdTech, technology sectors, consulting, or comparable settings overseeing complex portfolios of external technology vendors.
• Proficiency with portfolio and project delivery platforms such as Linear, Jira, or equivalent 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.

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 available immediately. The payment period is weekly.