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

What you will be doing

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• 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.

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What you won’t be doing

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• 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.

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Key responsibilities

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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.

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Basic requirements

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• 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.

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Nice-to-have requirements

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• 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.

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About 2 Hour Learning

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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.

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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.  

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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.

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2 Hour Learning is reprogramming learning for the AI era.

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Working with us

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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.

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

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Crossover Job Code: LJ-5669-US-COUNTRY-DirectorProgra.006