Director of Program Management
$400,000 USD/year ^{Pay is set based on global value, not the local market.

Most roles = hourly rate x 40 hrs x 50 weeks}($200 USD/hour)

Not accepting applications on crossover.com at this time.

Description

You've managed portfolios worth over $25 million, crafted dashboards, tackled issues, and attended countless meetings. Yet, you've never truly held the reins.

At 2 Hour Learning, we're redefining that narrative. Our mission is audacious: to craft the world's most efficient, AI-driven learning platform that compresses an entire school day into just two hours without compromising mastery or outcomes. To achieve this, we need a high-speed execution system that matches our ambition, and you're the one to build it.

This isn't about project management; it's about performance mastery. You'll be the architect and operator of an AI-driven control system for a $50 million EdTech portfolio. Say goodbye to endless meetings, as live dashboards take their place. Vendor scorecards will guide decisions on reallocations, replacements, or exits. You'll negotiate and enforce contracts. Every initiative flows through your bid process, and every deliverable is linked to academic impact. If a vendor falls short, your memos will decide their fate.

Here, we embrace speed, automation, and an intolerance for passivity. If you're tired of creating presentations that lead nowhere and are eager to own the tools, vendors, and execution outcomes that truly enhance student learning, you'll find the mandate, authority, and urgency you've been searching for with us.

What you will be doing

Spearheading a dynamic, AI-powered execution dashboard for over 25 initiatives—ensuring transparency, accountability, and tangible results.
Developing rubric-based vendor scorecards that prompt decisive actions: expanding work, adjusting scope, replacing, or terminating.
Conducting structured, competitive vendor evaluations for each new initiative—establishing clear scopes, budgets, and award justifications.
Crafting contracts with precise terms, performance alignment, and billing safeguards—eliminating loopholes and ambiguity.
Authoring memos that highlight vendor shortcomings, cite contract breaches, and recommend definitive actions—whether to offboard, renegotiate, or escalate.

What you will NOT be doing

Merely coordinating—this role demands ownership, not templates.
Allowing vendor issues to "bubble up"—you'll escalate, resolve, or replace.
Accepting vague contracts, missed deadlines, or uncertain billing.
Creating passive reports without actionable follow-up.
Delegating AI tasks to analysts—this is a hands-on, AI-centric role.

Key responsibilities

Design and manage the execution system that ensures vendor accountability, reallocates resources, and delivers timely, high-quality results across a $50 million EdTech portfolio.

Candidate requirements

5+ years in Program Management, Portfolio Management, or PMO leadership roles managing complex, multi-initiative portfolios.
Demonstrated ownership of $25M+ technology expenditures, including vendor selection, budget control, and delivery oversight.
Experience in conducting competitive bid processes and negotiating enforceable contracts.
Proficiency in developing and operating AI-driven execution dashboards (Linear, Jira, Notion) utilized by executives for decision-making, not just tracking.
Regular user of AI tools (e.g., GPT, Copilot, dashboards) to automate tasks, synthesize insights, and expedite delivery.
Proven ability to achieve results without playbooks—problem-solving, escalating issues, and taking ownership in high-ambiguity, high-stakes environments.
Strong executive communication skills, with a proven 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

Experience in launching or revamping a PMO or control system.
Familiarity with EdTech platforms or academic outcome metrics.
Exposure to legal, procurement, or contract governance in tech settings.

How it works

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