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
Description
You've managed portfolios worth over $25M, crafted dashboards, and tackled issues head-on. Yet, full control has always eluded you.
At 2 Hour Learning, that's about to change. We're pioneering the most efficient, AI-driven learning platform globally, transforming a full school day into just two hours without compromising mastery or outcomes. Our mission is audacious: empower students to learn twice as much in half the time. To achieve this, we need an execution system as dynamic as our goals, and you'll be the architect behind it.
This isn't mere project management—it's performance mastery. You'll design and manage the AI-enhanced control system for a $50M EdTech portfolio. That means real-time dashboards that replace meetings, vendor scorecards that dictate reallocations, replacements, or terminations, and contracts that you negotiate and enforce. Every new project is part of your bidding process, with each deliverable linked to academic impact. If a vendor falls short, your memos will determine the course of action.
We operate at lightning speed, automate relentlessly, and don't accept passivity. If you're weary of creating presentations that lead nowhere and are eager to control the tools, vendors, and execution outcomes that genuinely enhance student learning, you'll find the mandate, authority, and urgency you crave here.
What you will be doing
- Managing a live, AI-driven execution dashboard for 25+ ongoing initiatives—enhancing visibility, accountability, and results.
- Developing rubric-based vendor scorecards that prompt actions: increased workload, reduced scope, replacement, or termination.
- Leading structured, competitive vendor assessments for each new initiative—establishing clear scopes, budgets, and award justifications.
- Negotiating contracts with enforceable terms, performance alignment, and billing safeguards—eliminating loopholes and ambiguities.
- Crafting memos that highlight vendor shortcomings, cite contract breaches, and propose decisive actions—offboarding, renegotiating, or escalating.
What you will NOT be doing
- Merely coordinating instead of owning—this role has substance, not templates.
- Allowing vendor issues to "bubble up"—you escalate, resolve, or replace.
- Tolerating vague contracts, missed deadlines, or uncertain billing.
- Drafting passive reports without actionable follow-up.
- Delegating AI utilization to analysts—this is a hands-on, AI-centric role.
Key responsibilities
Create and operate the execution system that ensures vendor accountability, reallocates resources, and ensures on-time, high-quality delivery across a $50M EdTech portfolio.
Candidate 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
- 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
You will be working for
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