Program Director
$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 steered $25M+ portfolios, mastered dashboards, and tackled issues head-on. But true autonomy has eluded you—until now.

Welcome to 2 Hour Learning, where you'll revolutionize education with the most efficient AI-driven learning system. Our aim is audacious: double the learning in half the time. To achieve this, we need a dynamic execution system matching our ambition, and you're the architect.

This isn't about managing projects; it's about harnessing performance. You'll design and manage the AI-driven control system for a $50M EdTech portfolio. Imagine live dashboards replacing endless meetings, vendor scorecards prompting swift action, and contracts you negotiate and enforce. Every new project goes through your meticulous bid process, and every deliverable impacts academia. If a vendor falters, your decisive memos will set the course.

We thrive on speed and automation, rejecting passivity. If you're ready to move beyond meaningless presentations and take charge of the tools, vendors, and outcomes that genuinely enhance student learning, your search ends here with the mandate, authority, and urgency you've been seeking.

What you will be doing

Managing an AI-powered execution dashboard for over 25 active projects, ensuring transparency, accountability, and success.
Developing vendor scorecards based on rubrics to decide on expanding, reducing, replacing, or terminating engagements.
Conducting competitive vendor evaluations for new projects with clearly defined scopes, budgets, and award justifications.
Negotiating clear, enforceable contracts with performance alignment and billing safeguards—eliminating any ambiguity.
Crafting memos to address vendor shortcomings, highlight contract breaches, and recommend decisive actions like offboarding or renegotiation.

What you will NOT be doing

Merely coordinating—this role demands leadership, not templates.
Allowing vendor issues to "bubble up"—you address, resolve, or replace.
Accepting unclear contracts, missed deadlines, or vague billing.
Writing passive reports that lack actionable follow-up.
Delegating AI tasks to analysts—this is a direct, AI-centric role.

Key responsibilities

Design and implement an execution framework that ensures vendor accountability, reallocates resources effectively, and ensures timely, high-quality delivery across a $50M EdTech portfolio.

Candidate requirements

5+ years in Program Management, Portfolio Management, or PMO leadership roles managing complex, multi-project portfolios.
Demonstrated management of $25M+ technology budgets, including vendor selection, budget oversight, and delivery management.
Hands-on experience with competitive bid processes and contract negotiations.
Experience building and managing AI-driven execution dashboards (Linear, Jira, Notion) for executive decision-making.
Regular user of AI tools (e.g., GPT, Copilot, dashboards) for work automation, insight synthesis, and delivery acceleration.
Proven ability to achieve outcomes without predefined playbooks—problem-solving, escalating issues, and taking charge in uncertain, high-pressure environments.
Excellent executive communication skills, with experience influencing C-suite decisions through memos, dashboards, and vendor management.
Based in the US, open to 25% domestic travel, and eligible to work in the US without sponsorship.

Nice to have

Experience launching or overhauling a PMO or control system.
Knowledge of education tech platforms or academic outcome metrics.
Experience in legal, procurement, or contract governance within tech environments.

How it works

CROSSOVER'S PROCESS

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