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

You've built dashboards. Tracked milestones. Chased vendors. Flagged risks. But your reports hit a ceiling. You weren't the one making the calls.

2 Hour Learning is building an AI-powered education model designed to help students achieve a full day of academic progress in just two hours. Making that model work at scale requires dozens of initiatives, technology partners, contracts, and investment decisions to move in sync. Your job as Director of Program Management is to make the execution layer trustworthy enough for executives to act on it.

You will own the operating outputs behind those decisions: portfolio dashboards that expose slippage before it becomes a surprise, vendor scorecards tied to real contractual commitments, competitive bid packages that make trade-offs clear, and contract controls that prevent unsupported spend. AI will be part of your daily workflow, helping you standardize updates, detect anomalies, compare bids, analyze vendor performance, and validate invoices.

This is not a PMO role built around meetings, process compliance, or polished status decks. It is for an operator who wants their work to have consequences. When a vendor underperforms, your evidence should make that obvious. When spend drifts from the contract, your controls should catch it. When executives need to make a $5M decision, your outputs should give them the confidence to make it fast. If that sounds like the level of ownership you have been looking for, apply.

What You Will Be Doing

• Own portfolio-level dashboards across 10+ concurrent initiatives, using AI to standardize updates, detect slippage, expose blockers, and maintain a trusted executive view of delivery, budget, and risk
• Run recurring vendor performance reviews and maintain rubric-based scorecards that combine delivery, quality, cost, contractual commitments, and qualitative performance signals
• Lead competitive technology-vendor procurement, including structured bid packages, normalized comparisons, scoring rubrics, SOW development, and evidence-backed recommendations
• Govern contracts and invoices by tracking fee caps, milestones, acceptance criteria, and amendments, then validating invoices against signed terms before spend is approved
• Use AI daily to analyze portfolio data, detect anomalies, surface underperformance, draft decision-ready outputs, and reduce manual PMO administration
  
  

What You Won’t Be Doing

• Producing status reports that executives read but never use to make decisions
• Running a meeting-heavy PMO where coordination matters more than measurable execution
• Treating vendor management as relationship maintenance while missed commitments go unchallenged
• Passing contracts, SOWs, invoices, or procurement decisions to someone else because they look too commercial or technical
• Using AI as an occasional productivity trick instead of a core part of how you operate
  
  

Director Program Management Key Responsibilities

Produce reliable, AI-powered dashboards, scorecards, procurement packages, and contract controls that give executives the clarity and leverage to hold vendors accountable, control costs, and accelerate delivery across a $50M EdTech portfolio.

Basic Requirements

• Directly owned a portfolio of 10+ concurrent initiatives with at least $5M in budget responsibility, including authority over budget allocation, vendor selection, or initiative prioritization
• Managed 5+ external technology vendors at the same time, such as SaaS providers, AI/ML platforms, marketing agencies, or engineering firms
• Built and maintained portfolio-level dashboards covering metrics such as delivery health, budget burn versus forecast, milestone completion, and major risks or blockers
• Can point to a case where C-suite leaders used your portfolio data to make a go/no-go decision on a vendor renewal, budget reallocation, or initiative deprioritization
• Directly led competitive technology procurement, including structured bid evaluation, vendor scoring, negotiation, and selection
• Authored or co-authored SOWs with measurable deliverables, milestone payments, SLAs, acceptance criteria, or other performance-based terms
• Negotiated commercial terms such as pricing, penalties, fee caps, or exit clauses and enforced those terms through invoice validation or corrective action
• Strong written communication skills, with the ability to turn complex financial and operational data into concise recommendations executives can act on
• Able to analyze financial and vendor-performance data quickly enough to recommend optimization, reallocation, or vendor elimination
• Able to work US business hours
  
  

Nice-to-have Requirements

• Experience using AI-enabled dashboards, anomaly detection, predictive alerts, or natural-language analysis in portfolio management
• Experience in EdTech, technology, consulting, or another environment managing complex portfolios of external technology partners
• Fluency with portfolio and delivery tools such as Linear, Jira, or similar 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.

Here’s How They’re Fixing It.

There is so much to cover for this exciting role, and space here is limited. Hit the Apply button if you found this interesting and want to learn more. We look forward to meeting you!

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 www.crossover.com/help-and-faqs for more details on this topic.

Crossover Job Code: LJ-5669-BR-COUNTRY-DirectorProgra

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