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2 Hour Learning seeks a technical product leader with the expertise to architect and modernize our AI-driven learning ecosystem. This position demands someone capable of functioning at CTO-level technical depth while maintaining sharp product vision—applying both to transform student outcomes at scale.Where others append AI to conventional education frameworks as an add-on, we've taken a fundamentally different approach: constructing an entirely new school model anchored in AI and learning science, eliminating the limitations inherent in traditional classrooms. The results speak plainly—our students achieve multiple 4s and 5s on AP exams, demonstrate multi-year academic advancement within single academic years, and routinely exceed their own performance expectations. When AI serves as the foundational operating system for learning, student achievement reaches new heights.This position diverges from conventional product management centered on feedback cycles and incremental releases. You will hold executive-level technical product ownership, commanding the architecture, technical roadmap, and AI integration across our complete learning platform. Your mandate includes making critical technical trade-offs that keep our products lean, scalable, and laser-focused on student outcome improvement. You'll combine CTO-level thinking with product entrepreneurship, merging engineering discipline with learning science to drive continuous innovation.If you possess both the ambition to lead education's technical transformation and the execution discipline to deliver on it, we invite your application.



This role offers the prospect to architect the future of learning.What You Will Be DoingCultivating and applying comprehensive education product expertise to inform strategic directionCreating technical specifications that resolve critical technical decisions while prioritizing simplicity, efficiency, and sustainable architectureDeploying generative AI capabilities to automate engineering workflows and reduce manual effort, consistent with our strategic commitment to operational efficiencyWhat You Won’t Be DoingManaging people as your primary function; this role centers on your technical and business judgmentSpending time on meetings, committees, or administrative overhead; we've automated management tasks to free you for value-creation through direct contributionProposing abstract strategies disconnected from execution; your guidance must stemfrom product-level understandingVice President Of Product Engineering Key ResponsibilitiesServe as the CTO for one or more education products, owning core technical capabilities and generating business value through flawless execution and strategic leadershipBasic Requirements7+ years of experience making critical architecture and design decisions on software projects, including application of architecture design patterns or major open source technologies4+ years of experience in roles with complete technical and delivery ownership over a revenue-generating productExperience leveraging AI agents to design, implement, and test software products or featuresWorking with us It 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

Apply on Kit Job: kitjob.ca/job/2fsnlf

📌 Vice President Of Product Engineering, 2 Hour Learning (Remote) - $400,000/Year Usd (Toronto)
🏢 Crossover
📍 Toronto