Vice President Of Product Engineering
Crossover
About the role
About
2 Hour Learning seeks a technical product leader with the expertise to serve as the architect of our AI‑powered learning ecosystem. This position is designed for someone who combines the technical depth of a CTO with the product acumen to drive transformational outcomes, applying both to unlock student potential at scale never before achieved.
Where most organizations treat AI as a supplemental layer on top of conventional education systems, we have taken a fundamentally different approach: reconstructing the school experience from its foundation using AI and learning science to eliminate the limitations inherent in traditional classroom structures. Our results speak for themselves — students achieve multiple 4s and 5s on AP exams, demonstrate multi‑year academic advancement within a single year, and regularly exceed their own projected outcomes. When AI serves as the foundational operating system for learning, student performance reaches extraordinary levels.
This is not a conventional product management position centered on user feedback cycles or iterative feature releases. This is an executive‑level technical product ownership role in which you will control the architecture, technical direction, and AI integration across our complete learning platform. Your responsibility will be to navigate the complex technical trade‑offs that keep our products efficient, scalable, and unwaveringly centered on student achievement. You will operate with the strategic mindset of a CTO while executing with the agility of a product entrepreneur, merging engineering discipline with learning science principles to deliver continuous innovation.
If you are prepared to lead the technical transformation of education and possess the operational discipline to realize that vision, we invite your application. This opportunity allows you to shape the future of how students learn.
Responsibilities
- Build and maintain deep technical expertise in education products to inform strategic direction.
- Create technical specifications that resolve critical technical decisions while prioritizing simplicity, operational efficiency, and sustainable long‑term design.
- Deploy generative AI capabilities to automate and optimize engineering workflows, consistent with the organizational goal of minimizing manual effort.
- Serve as the CTO for one or more education products, owning technical competencies and generating business impact through flawless execution and strategic leadership.
What You Won’t Be Doing
- Functioning solely as a people manager; this role demands both business insight and technical expertise.
- Spending time in meetings, committees, or administrative overhead; automated management systems free you to concentrate on delivering tangible business impact through direct contribution.
- Proposing high‑level strategy without actionable implementation plans; your guidance must be grounded in product‑level understanding.
Basic Requirements
- 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.
- 4+ years of experience in roles with complete technical and delivery accountability for a revenue‑generating product.
- Experience leveraging AI agents to design, implement, and test software products or features.
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.
Students consistently rank in the top 1‑2% nationally, and the top 20% achieve an astonishing 6.5× growth, proving that smarter learning is possible. At 2 Hour Learning, talent and performance matter.
The company offers a dynamic, on‑campus and remote‑friendly environment where innovators, educators, and AI specialists can be part of fixing a broken school system. 2 Hour Learning is reprogramming learning for the AI era.
Working with Us
- Full‑time (40 hours per week), long‑term position.
- Immediately available; requires entering into an independent contractor agreement with Crossover as a Contractor of Record.
- Compensation: $200 USD/hour, equating to $400,000 USD/year (assuming 40 hours/week and 50 weeks/year).
Requirements
- 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
- 4+ years of experience in roles with complete technical and delivery accountability for a revenue-generating product
- Experience leveraging AI agents to design, implement, and test software products or features
Responsibilities
- Building and maintaining deep technical expertise in education products to inform strategic direction
- Creating technical specifications that resolve critical technical decisions while prioritizing simplicity, operational efficiency, and sustainable long-term design
- Deploying generative AI capabilities to automate and optimize engineering workflows, consistent with the organizational goal of minimizing manual effort
- Serve as the CTO for one or more education products, owning technical competencies and generating business impact through flawless execution and strategic leadership
Skills
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