🚀 Program Director, 2 Hour Learning (Remote) - $400,000/year USD

Pay

$200.00/hr

Overview

Are you ready to take the reins of a $50M EdTech portfolio, shaping the future of AI-driven learning? At 2 Hour Learning, you won’t just manage projects; you’ll revolutionize them.

What You Will Be Doing

• Commanding a sophisticated AI-driven execution dashboard to ensure visibility and accountability across 25+ initiatives.
• Crafting vendor scorecards that drive decisive actions, from extensions to terminations.
• Leading competitive vendor evaluations to define sharp scopes and budgets.
• Negotiating ironclad contracts that align performance with payment.
• Composing strategic memos to address vendor non‑compliance and propose impactful solutions.

What You Won’t Be Doing

• Merely coordinating—this role empowers you to take charge.
• Allowing vendor issues to linger—you’ll address them head‑on.
• Accepting vague contracts and timelines.
• Creating reports that lack actionable insights.
• Relying on others for AI integration—this is your domain.

Program Director Key Responsibilities

Drive the success of a cutting‑edge execution system that ensures vendor accountability and resource optimization, delivering timely, top‑quality outcomes for a $50M EdTech portfolio.

Basic Requirements

• 5+ years in Program Management, Portfolio Management, or PMO leadership roles overseeing complex, multi‑initiative portfolios.
• Proven ownership of $25M+ technology spend, including vendor selection, budget control, and delivery oversight.
• Hands‑on experience running competitive bid processes and negotiating enforceable contracts.
• Built and operated AI‑powered execution dashboards (Linear, Jira, Notion) used by execs for decision‑making—not just tracking.
• Daily user of AI tools (e.g., GPT, Copilot, dashboards) to automate work, synthesize insights, and accelerate delivery.
• Proven ability to drive outcomes without playbooks—solving problems, escalating issues, and taking ownership in high‑ambiguity, high‑stakes settings.
• Strong executive communication skills, with a track record of influencing C‑suite decisions through memos, dashboards, and vendor oversight.
• US‑based, open to 25% domestic travel, and eligible to work in the US without sponsorship.

Nice‑to‑have Requirements

• Prior experience launching or overhauling a PMO or control system.
• Familiarity with education tech platforms or academic outcome metrics.
• Exposure to legal, procurement, or contract governance in tech environments.

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 6.5× growth, they’re proving that smarter learning is possible. At 2 Hour Learning, it’s talent and performance that matter.

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 $200 USD/hour, which equates to $400,000 USD/year assuming 40 hours per week and 50 weeks per year. The payment period is weekly.

Seniority level

• Executive

Employment type

• Full‑time

Job function

• Business Development, Engineering, and Project Management
• Industries: Education Administration Programs, Higher Education, and Non‑profit Organizations