Youve run $25M+ portfolios. Built dashboards. Escalated issues. Sat in meetings. But youve never had full control.

At 2 Hour Learning, that changes. Were 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 youll build it.

This isnt project management. Its performance control. Youll 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 dont tolerate passivity. If youre tired of producing decks that go nowhere and are ready to own the tools, vendors, and execution outcomes that actually drive student learning, youll find the mandate, authority, and urgency youve been looking for here.

What You Will Be Doing

• Owning a live, AI-powered execution dashboard for 25+ active initiativesdriving 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 initiativedefining clear scopes, budgets, and award rationale.
• Negotiating contracts with enforceable terms, performance alignment, and billing protectionsno loopholes, no fuzziness.
• Writing memos that flag vendor failures, cite contract violations, and recommend decisive actionoffboard, renegotiate, or escalate.
  
  

What You Wont Be Doing

• Coordinating instead of owningthis role has teeth, not templates.
• Letting vendor problems bubble upyou escalate, fix, or replace.
• Accepting ambiguous contracts, overdue milestones, or billing guesswork.
• Writing passive reports with no follow-up action.
• Delegating AI use to analyststhis is a hands-on, AI-native role.
  
  

Program Management Officer Key Responsibilities

Build and run the execution system that enforces vendor accountability, reallocates resources, and drives on-time, high-quality delivery across a $50M EdTech portfolio.

Basic 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-makingnot 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 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 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 one-size-fits-all model and replacing it with AI-driven personalized learning that helps kids master academics in just two hours a day.

With students consistently ranking in the top 1-2% nationally and the top 20% achieving an astonishing 6.5x growth, theyre proving that smarter learning is possible. At 2 Hour Learning, its talent and performance that matter.

They offer a dynamic, on-campus and remote-friendly environment where innovators, educators, and AI specialists can be a part of fixing a broken school system.

2 Hour Learning is reprogramming learning for the AI era.

Heres How Theyre Fixing It.

There is so much to cover for this exciting role, and space here is limited. Hit the Apply button if you found this interesting and want to learn more. We look forward to meeting you!

Working with us

This is a full-time (40 hours per week), long-term position. The position 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 $200 USD/hour, which equates to $400,000 USD/year assuming 40 hours per week and 50 weeks per year. The payment period is weekly. Consult www.crossover.com/help-and-faqs for more details on this topic.

Crossover Job Code: LJ-5564-US-Aurora-ProgramManagem.004