Vice President of Product Engineering, Learning; Remote

Vice President of Product Engineering – 2 Hour Learning (Remote)

Join Crossover as the executive‑level technical product leader responsible for driving the modernization of our AI‑driven learning ecosystem. Your role will combine the technical depth of a CTO with strategic vision to unlock student potential at scale.

$200.00/hr – $200.00/hr

This position demands deep technical expertise, strategic leadership, and a relentless focus on educational impact. Working at the intersection of AI, learning science, and product execution, you will own architecture, AI integration, and technical strategy across the entire platform. You will make critical trade‑offs to keep our products lean and scalable, while delivering breakthroughs that improve student outcomes.

• Lead as the CTO for one or more education products, driving strategy and execution.
• Author technical specifications to enforce simplicity, efficiency, and sustainable design.
• Deploy generative AI technologies to automate engineering workflows and minimize manual effort.
• Integrate data‑driven learning science insights into product decisions.
• Guide cross‑functional teams through technical decisions and road‑mapping.

• Focusing purely on people management; this role emphasizes technical judgment.
• Spending time on unnecessary meetings or administrative overhead.
• Proposing high‑level strategies detached from execution.

• Significant or strong interest in data‑driven learning science.
• 7+ years of experience making architectural and design decisions on software projects.
• 2+ years of experience with cloud computing services, primarily AWS.
• 4+ years of full ownership of a revenue‑generating product.
• Experience developing AI/Generative‑AI features that enhance product value.
• Experience applying Generative AI to streamline work processes.

2 Hour Learning is reimagining education with AI‑driven personalized learning that helps students master academics in just two hours a day. Students achieve top 1‑2% national rankings, and 20% see a 6.5x growth in competency.

This is a full‑time (40 hrs/week) contractor role with a $200/hr compensation, paid weekly. The position is immediately available.

Executive

Full‑time

Engineering and Product Management