Vice President of Product Engineering, Learning; Remote

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

Join to apply for the Vice President of Product Engineering, 2 Hour Learning (Remote) - $400,000/year USD role at Crossover

$200.00/hr - $200.00/hr

We are seeking a deeply technical product leader to spearhead the modernization of our AI-powered learning ecosystem at 2 Hour Learning. This position requires someone with the technical depth to operate at a CTO level, the strategic vision to drive transformational product evolution, and the commitment to apply these capabilities toward unlocking student potential at scale previously unimaginable. While most organizations treat AI as an add-on to conventional educational frameworks, 2 Hour Learning has taken a fundamentally different approach: we have reconstructed the entire school model, leveraging AI and learning science to eliminate the limitations inherent in traditional classrooms.

The results speak for themselves—our students achieve multiple 4s and 5s on AP examinations, 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 extraordinary levels. This position differs significantly from traditional product management roles centered on customer feedback cycles or iterative feature releases.

Instead, this is an executive-level technical product ownership role where you will control the architecture, technical roadmap, and AI integration across our complete learning platform. Your responsibility includes making critical technical tradeoffs that keep our products streamlined, scalable, and laser-focused on student outcome improvement. You will combine the strategic thinking of a CTO with the execution velocity of a product entrepreneur, merging engineering discipline with learning science principles to generate continuous innovation.

If you are prepared to lead the technical transformation of education and possess the operational determination to realize that vision, we invite your application. This represents your chance to shape the future of learning.

• Building and applying comprehensive education product expertise to inform strategic direction
• Creating technical specifications that drive critical technical decisions while prioritizing simplicity, operational efficiency, and sustainable long-term design
• Deploying generative AI capabilities to automate and optimize engineering workflows, supporting the organizational objective of minimizing manual intervention

• Serving purely as a people manager; this role demands substantial business insight and technical judgment
• Spending time on meetings, committee work, and administrative overhead; we have streamlined management processes to enable your focus on hands-on value creation
• Proposing high-level strategies disconnected from execution; your guidance must derive from product-level understanding

• Serve as the CTO for one or more education products, commanding core technical competencies and delivering business impact through flawless execution and strategic leadership

• Substantial experience or demonstrated interest in data-driven learning science
• 7+ years of experience making critical architecture and design decisions on software initiatives, including 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 accountability for a revenue-generating product
• Proven experience building product features that leverage advanced Generative AI capabilities
• Demonstrated experience applying Generative AI to streamline work processes

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…