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Job Title


Vice President of Product Engineering, 2 Hour Learning (Remote) - $400,000/year


Company : Crossover


Location : Toronto, Ontario


Created : 2026-02-03


Job Type : Full Time


Job Description

Overview This role is for a technical product leader prepared to drive the reinvention of education through AI. 2 Hour Learning seeks an architect with the depth to lead the modernization of our AI-powered learning ecosystem. You will need the technical expertise to function as a CTO, the strategic vision to catalyze transformational change, and the commitment to deploy these capabilities to unlock student potential at scale. While most organizations add AI to conventional education systems as a superficial enhancement, 2 Hour Learning has pursued a fundamentally different approach: we have reconstructed the entire school model, leveraging AI and learning science to eliminate the limitations of the traditional classroom. Our students dont merely progress they excel, earning multiple 4s and 5s on AP exams, demonstrating multi-year academic advancement within a single year, and regularly surpassing their own projected outcomes. We have validated that when AI serves as the foundational operating system for learning, student performance accelerates dramatically. This is not a conventional product management position centered on customer feedback cycles or gradual feature rollouts. This is an executive-level technical product ownership role in which you will control the architecture, technical roadmap, and AI integration across our complete learning platform. You will make the difficult technical trade-offs necessary to keep our products lean, scalable, and relentlessly oriented toward student outcome improvement. You will think with the rigor of a CTO while executing with the agility of a product entrepreneur, fusing engineering discipline with learning science principles to drive continuous innovation. If you are prepared to lead the technical transformation of education and possess the operational discipline to support that vision, we invite your application. This is your chance to shape the future of learning. What You Will Be Doing Sustaining and demonstrating comprehensive education product expertise to inform strategic decisions Creating technical specifications that resolve critical technical decisions and emphasize simplicity, efficiency, and long-term sustainability Deploying generative AI technologies to automate and optimize engineering workflows, consistent with the strategic objective of minimizing manual effort What You Wont Be Doing Pure people management; this position demands your business judgment and technical expertise as primary drivers Spending time on meetings, committees, and administrative overhead; we have automated management burdens to enable focus on delivering business value through direct contribution High-level strategic recommendations without actionable implementation guidance; your proposals must be grounded in product-level detail Vice President Of Product Engineering Key Responsibilities Serve as the CTO for one or more education products, owning core technical competencies and generating business value through flawless execution and strategic leadership Basic Requirements Substantial experience or demonstrated interest in data-driven learning science 7+ years of experience making critical architecture and design decisions on software projects, including the application of architecture design patterns or major open source technologies 2+ years of experience making design decisions that involve cloud computing services (primarily AWS) 4+ years of experience in roles with complete technical and delivery ownership of a revenue-generating product Experience developing product features that leverage advanced use of Generative AI Experience applying Generative AI to streamline work processes 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-5590-CA-Toronto-VicePresidento.017 #J-18808-Ljbffr