L2 Support Engineer

L2 Support Engineer at Crossover

Educational support systems face increasing complexity, demanding faster, more reliable service for schools, students, and families. Today's schools need immediate, AI-powered responses across diverse platforms like learning management systems, student information systems, devices, and administrative workflows. However, most support organizations struggle with fragmented tools and manual processes that buckle under pressure.

Crossover tackles this by embedding AI-enhanced "cyborg" support agents within a live educational operations environment. As an L2 Support Engineer, you will directly influence this system's evolution. Every resolution you provide refines future automation, each root cause identified shapes processes and policies, and every solved edge case strengthens outcomes for thousands of students and educators.

This role involves production-grade, hands-on troubleshooting in a live service setting. You will investigate ambiguous, multi-party failures spanning learning platforms, SIS infrastructure, identity management, network systems, and operational processes. You'll leverage AI to generate hypotheses, validate scenarios, and expedite resolutions, documenting the human reasoning that trains both systems and colleagues. Proactively surfacing patterns will convert isolated fixes into scalable, cross-team enhancements.

This is not first-line triage, simple checkbox execution, or a "forward and forget" role. If you thrive when documentation is sparse, issues cross engineering, operations, and academic domains, and you can switch between deep technical analysis and precise stakeholder communication, this role is for you.

What You Will Be Doing

• AI-Augmented Customer Resolutions: Investigate complex tickets escalated by AI systems, apply human judgment to challenges AI cannot yet address, and then enhance the AI system to close those capability gaps.

What You Won’t Be Doing

• Taking two full months to reach productivity; you will be expected to ramp up on multiple products within your first month (we acknowledge this is demanding).
• Depending on your managers for assistance; if you are not skilled at self-unblocking, you will likely find this role challenging.

L2 Support Engineer Key Responsibilities

• Combine technical human judgment and AI capabilities to provide exceptional customer support, concentrating on complex issues that AI cannot yet fully address.

Basic Requirements

• Must be located in North or South America.
• At least 3 total years of experience in a technical customer support role.
• Basic coding skills for the purpose of troubleshooting/bug fixes.
• Troubleshooting Skills: Explaining complex issues in simple terms, demonstrating strong problem understanding, recommending relevant troubleshooting strategies, proposing multiple solution paths, and showing attention to detail.

About Alpha School

Want to join a learning rebellion that’s transforming the traditional classroom? Alpha School is on a mission to reshape education with a bold approach that harnesses AI to accelerate learning and unleash student potential.

They don’t play by the old rules. Alpha is creating a new paradigm where students master core academics in just two hours a day, freeing up time for hands-on, passion-driven learning that truly prepares them for the real world.

Alpha School is rewriting the rules of education.

Sounds too good to be true? It’s not. 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 $30 USD/hour, which equates to $60,000 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.

Key skills/competency

• Technical Support
• AI Augmentation
• Troubleshooting
• Customer Resolution
• System Analysis
• Process Improvement
• Basic Coding
• Educational Technology
• Problem Solving
• Stakeholder Communication