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

You've monitored progress. Maintained trackers. Followed up with vendors. Documented risks. But the final decisions weren't yours to make. That changes at 2 Hour Learning. We're constructing the world's most efficient AI-powered learning system—condensing an entire school day into two hours while preserving educational outcomes. Supporting this mission is a $50M portfolio of rapidly evolving EdTech projects. Your role will determine whether these projects deliver on schedule, within budget, and to standard. You'll run the operational infrastructure that ensures vendor accountability. Build executive-grade dashboards that deliver real-time visibility. Develop vendor scorecards that trigger decisions. Execute structured procurement processes and verify billing accuracy down to the line item. When a vendor falls behind, you surface it. When an invoice doesn't reconcile, you escalate it. Your outputs won't inform strategy—they'll define it. This role is designed for operators seeking authority, not adjacency. If you're prepared to assume a position where precision is non-negotiable, AI accelerates your impact, and your analysis directly influences which vendors expand, pivot, or exit, let's talk. What You Will Be Doing • Own and update live, AI-enhanced dashboards spanning 25+ initiatives—guaranteeing data integrity, transparency, and schedule adherence • Facilitate vendor reviews, construct rubric-driven scorecards, and generate insights that inform budget reallocation, scope reduction, or vendor transitions • Prepare dual-bid procurement documentation with side-by-side vendor analysis and defined scopes—enabling informed vendor decisions • Monitor contract compliance and invoice accuracy—confirming every expense maps to agreed deliverables, caps, and executed agreements • Leverage AI tools daily to identify discrepancies, generate reports, follow up on action items, and enhance all deliverables What You Won’t Be Doing • Attending status meetings while projects drift unnoticed in the background • Outsourcing AI-driven tasks to junior staff or depending on others to maintain system accuracy • Allowing invoice discrepancies or vendor delays to pass without escalation • Generating reports that circulate without influencing outcomes or prompting decisions • Operating on intuition or approximation—your work is data-driven and executive-ready Director Of Vendor Program Management Key Responsibilities Deliver the dashboards, scorecards, procurement documentation, and contract oversight that fuel a $50M operational system and enforce continuous vendor performance accountability. Basic Requirements • Direct ownership of multi-initiative program or portfolio execution ($5M+ in scope), including hands-on vendor management • Designed and sustained dashboards, scorecards, or monitoring systems that senior leadership depended on—not solely operational teams • Proven experience facilitating vendor meetings, preparing bid documentation, and contributing to contract negotiation cycles • Practical understanding of contracts, statements of work, and invoicing—with demonstrated ability to identify and escalate inconsistencies • Exceptional written communication—your documentation drives action, not additional discussion • Routine application of AI tools to streamline, evaluate, and expedite execution • Located in the US, available for 25% domestic travel, and authorized to work in the US without requiring visa sponsorship Nice-to-have Requirements • Background in EdTech, management consulting, or high-velocity operational environments • Proficiency with platforms such as Linear, Notion, Jira, or bespoke AI-powered dashboards • Prior involvement with vendor performance scorecards 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-Cook-DirectorofVend.007 Apply tot his job