Job Description

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

Join Trilogy as the Program Director of 2 Hour Learning, overseeing a $50M EdTech portfolio and driving AIpowered learning solutions.

Base pay range

$200.00/hr $200.00/hr

What You Will Be Doing

• Command a sophisticated AIdriven execution dashboard ensuring visibility and accountability across 25+ initiatives.
• Craft vendor scorecards that drive decisive actions, from extensions to terminations.
• Lead competitive vendor evaluations to define sharp scopes and budgets.
• Negotiate ironclad contracts that align performance with payment.
• Compose strategic memos addressing vendor noncompliance and proposing impactful solutions.

What You Wont Be Doing

• Merely coordinatingthis role empowers you to take charge.
• Allowing vendor issues to lingeryoull address them headon.
• Accepting vague contracts and timelines.
• Creating reports that lack actionable insights.
• Relying on others for AI integrationthis is your domain.

Program Director Key Responsibilities

Drive the success of a cuttingedge execution system that ensures vendor accountability and resource optimization, delivering timely, topquality outcomes for a $50M EdTech portfolio.

Basic Requirements

• 5+ years in Program Management, Portfolio Management, or PMO leadership overseeing complex, multiinitiative portfolios.
• Proven ownership of $25M+ technology spend, including vendor selection, budget control, and delivery oversight.
• Handson experience running competitive bid processes and negotiating enforceable contracts.
• Built and operated AIpowered execution dashboards (Linear, Jira, Notion) used by execs for decisionmakingnot 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 playbookssolving problems, escalating issues, and taking ownership in highambiguity, highstakes settings.
• Strong executive communication skills, with a track record of influencing Csuite decisions through memos, dashboards, and vendor oversight.
• USbased, open to 25% domestic travel, and eligible to work in the US without sponsorship.

Nicetohave 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 doesnt have to be. Theyre tearing down the outdated onesizefitsall model and replacing it with AIdriven personalized learning that helps kids master academics in just two hours a day. With students consistently ranking in the top 12% nationally and the top 20% achieving an astonishing 6.5x growth, theyre proving that smarter learning is possible.

Working with us

This is a fulltime (40hours per week), longterm position. The role 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 $200USD/hour, which equates to $400,000USD/year assuming 40hours per week and 50 weeks per year. The payment period is weekly.

Seniority level

Executive

Employment type

Fulltime

Job function

Business Development, Engineering, and Project Management

Industries

Education Administration Programs, Higher Education, and Nonprofit Organizations

Job Tags

Similar Jobs