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

You've tracked timelines. Built status reports. Monitored vendor deliverables. Escalated blockers. But the final decisions weren't yours to make. That changes at 2 Hour Learning. We're constructing the world's most efficient AI-driven learning platform—condensing an entire school day into two hours while preserving educational outcomes. Supporting that mission is a $50M portfolio of rapidly evolving EdTech programs. Your role will determine whether these programs deliver on schedule, within budget, and to standard. You'll run the operational backbone that enforces vendor accountability. Build executive-grade dashboards updated in real time. Create vendor scorecards that trigger decisions. Manage competitive bidding cycles and verify every invoiced charge. When a vendor falls short, you surface it. When billing doesn't match scope, you escalate it. Your outputs won't just inform leadership—they'll steer action. This position is built for operators seeking accountability, not advisory roles. If you're prepared to move into a function where precision counts, AI amplifies your impact, and your analysis directly influences which vendors are retained, expanded, or replaced, let's talk. What You Will Be Doing

• Sustain real-time, AI-enabled dashboards spanning 25+ initiatives—guaranteeing data integrity, transparency, and schedule adherence
• Conduct vendor reviews, design rubric-driven scorecards, and generate insights that inform budget shifts, scope reductions, or vendor transitions
• Prepare dual-vendor procurement packages featuring side-by-side evaluations and precise scope definitions—facilitating vendor decisions
• Monitor contract compliance and invoice accuracy—confirming every charge corresponds to documented deliverables, limits, and agreements
• Leverage AI tools daily to identify discrepancies, generate documentation, request updates, and enhance all deliverables

What You Won’t Be Doing

• Attending status meetings while projects drift off-track without intervention
• Assigning AI execution to junior staff or depending on others to maintain system accuracy
• Overlooking invoice discrepancies or vendor performance gaps
• Creating reports that circulate but trigger no decisions or corrective measures
• Operating on assumptions or instinct—all your work is data-driven and leadership-ready

Director Program Management Key Responsibilities Deliver the dashboards, scorecards, procurement frameworks, and contract oversight that sustain a $50M operational system and enforce continuous vendor performance standards. Basic Requirements

• Direct ownership of multi-program execution or portfolio management ($5M+ in scope), including hands-on vendor coordination
• Developed and sustained dashboards, scorecards, or monitoring platforms used by executive leadership—not limited to operational teams
• Track record managing vendor meetings, preparing competitive bid materials, and contributing to contract processes
• Practical understanding of contracts, statements of work, and invoices—capable of identifying and escalating discrepancies
• Excellent written communication—your documentation drives action, not additional discussion
• Routine application of AI tools to streamline tasks, perform analysis, and improve speed of delivery
• US-based, willing to travel domestically up to 25%, and authorized to work in the US without requiring visa sponsorship

Nice-to-have Requirements

• Background in EdTech, consulting, or high-velocity operational environments
• Hands-on experience with platforms such as Linear, Notion, Jira, or proprietary AI dashboard systems
• Prior involvement with vendor scoring frameworks or enterprise-level 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.006