Director Program Management, 2 Hour Learning (Remote) - $200,000/year USD

You've tracked milestones. Built dashboards. Chased down vendors. Flagged risks before they became emergencies. But your analysis never crossed into decision-making—you reported, someone else acted. That changes at 2 Hour Learning. We're engineering the world's most efficient AI-powered learning system—condensing a full school day into two hours while preserving educational outcomes. Supporting that mission is a $50M portfolio of high-velocity EdTech projects. Your execution will determine whether those projects deliver on time, within budget, and to standard. You'll run the operational machinery behind vendor accountability. Build dashboards executives depend on in real time. Develop vendor scorecards that lead to tangible action. Manage structured procurement processes and verify every invoiced dollar. When a vendor underperforms, you detect it. When billing doesn't align, you surface it. Your outputs don't simply inform—they drive action. This role is designed for operators seeking ownership over observation. If you're prepared to enter a position where precision is non-negotiable, AI amplifies your capacity, and your contributions directly influence which vendors continue, expand, or exit—we want to meet you. What You Will Be Doing

• Operate live, AI-enhanced dashboards spanning 25+ initiatives—guaranteeing precision, transparency, and deadline adherence
• Conduct vendor check-ins, develop rubric-driven scorecards, and generate insights that inform scope reductions, resource shifts, or vendor exits
• Prepare dual-bid procurement packages featuring structured comparisons and defined scopes—enabling vendor selection decisions
• Monitor contract and invoice accuracy—confirming every expenditure matches deliverables, caps, and signed agreements
• Leverage AI daily to identify outliers, generate reports, follow up on updates, and enhance all deliverables

What You Won’t Be Doing

• Attending meetings while projects drift quietly off course in the background
• Assigning AI-related tasks to analysts or relying on others to maintain system currency
• Allowing billing discrepancies or vendor delays to pass without escalation
• Creating status reports that neither inform choices nor trigger action
• Operating on instinct or intuition—your work is data-driven and boardroom-ready

Director Program Management Key Responsibilities Deliver the dashboards, scorecards, bid packages, and contract governance that fuel a $50M execution engine and enforce real-time vendor performance standards. Basic Requirements

• Led execution of a multi-initiative program or portfolio ($5M+ in scope), involving direct vendor management
• Designed and maintained dashboards, scorecards, or tracking systems used by executives—not solely internal teams
• Conducted vendor check-ins, prepared bid packages, and contributed to contracting processes
• Practical knowledge of contracts, SOWs, and invoices—capable of identifying and escalating inconsistencies
• Excellent written communication—your documentation drives decisions, not additional discussion
• Daily application of AI tools to automate, assess, and expedite delivery
• Located in the US, willing to travel domestically 25% of the time, and authorized to work in the US without visa sponsorship

Nice-to-have Requirements

• Background in EdTech, consulting, or high-tempo operational environments
• Working knowledge of platforms such as Linear, Notion, Jira, or bespoke AI dashboards
• Prior experience with vendor scorecards or large-scale procurement workflows

About 2 Hour Learning Education is broken, but 2 Hour Learning is proving it doesn’t have to be. They’re 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, they’re proving that smarter learning is possible. At 2 Hour Learning, it’s 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.Here’s How They’re 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 $100 USD/hour, which equates to $200,000 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-5669-US-Austin-DirectorProgra.005