Program Management Officer $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
Not accepting applications on crossover.com at this time.
Description
You’ve run $25M+ portfolios. Built dashboards. Escalated issues. Sat in meetings. But you’ve never had full control.
At 2 Hour Learning, that changes. We’re building the most efficient, AI-accelerated learning system on the planet. We're compressing a full school day into just two hours, without sacrificing mastery or outcomes. Our mission is bold: enable students to learn twice as much, in half the time. To do that, we need an execution system that runs as fast as our ambition, and you’ll build it.
This isn’t project management. It’s performance control. You’ll architect and operate the AI-powered control system for a $50M EdTech portfolio. That means live dashboards that replace meetings. Vendor scorecards that lead to reallocations, replacements, or exits. Contracts you negotiate and enforce. Every new initiative runs through your bid process. Every deliverable is tied to academic impact. If a vendor underdelivers, your memos make the call.
We move fast. We automate everything. And we don’t tolerate passivity. If you’re tired of producing decks that go nowhere and are ready to own the tools, vendors, and execution outcomes that actually drive student learning, you’ll find the mandate, authority, and urgency you’ve been looking for here.
What you will be doing
- Owning a live, AI-powered execution dashboard for 25+ active initiatives—driving visibility, accountability, and outcomes.
- Building rubric-based vendor scorecards that trigger action: more work, less scope, replacement, or exit.
- Running structured, competitive vendor evaluations for every new initiative—defining clear scopes, budgets, and award rationale.
- Negotiating contracts with enforceable terms, performance alignment, and billing protections—no loopholes, no fuzziness.
- Writing memos that flag vendor failures, cite contract violations, and recommend decisive action—offboard, renegotiate, or escalate.
What you will NOT be doing
- Coordinating instead of owning—this role has teeth, not templates.
- Letting vendor problems “bubble up”—you escalate, fix, or replace.
- Accepting ambiguous contracts, overdue milestones, or billing guesswork.
- Writing passive reports with no follow-up action.
- Delegating AI use to analysts—this is a hands-on, AI-native role.
Key responsibilities
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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Prove real-world job skills.
Interview with the hiring manager.
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Pass proctored test.
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