L2 Support Engineer

Educational support systems are struggling under mounting complexity as demands from students, families, and institutions accelerate. Institutions increasingly require real-time, AI-powered responses spanning learning platforms, student information systems, devices, and operational processes. Yet most teams remain hampered by disconnected tools, manual handoffs, and fragile workflows that crumble when tested in practice.

We address this challenge through a radically different approach: AI-enhanced "cyborg" agents functioning at the heart of a dynamic education environment. In this position, you will influence how the system evolves. Each resolution refines future automation, each root cause investigation shapes process and policy, and each outlier you decode improves outcomes for thousands of learners and staff.

This is direct, production-level problem resolution within a service context. You will investigate unclear, multi-party failures spanning learning tools, SIS platforms, identity infrastructure, networks, and operational procedures; use AI to form hypotheses, validate theories, and speed up resolution; capture the human logic that instructs both technology and colleagues; and proactively surface patterns that convert isolated fixes into sustainable, organization-wide gains.

This is not about routing tickets, executing scripts, or deferring problems upward. If you excel when information is sparse, when challenges bridge engineering, operations, and instruction, and when you can transition from technical diagnosis to stakeholder coordination without sacrificing precision, this role will suit you.

What You Will Be Doing

• AI-Augmented Customer Resolutions: Examine complex cases escalated by AI platforms, contribute human judgment where AI is insufficient, and subsequently enhance the AI system to close those gaps

What You Won’t Be Doing

• Spending two full months onboarding; you will be expected to achieve proficiency across multiple products in the first month (we recognize this pace is demanding)
• Depending on your managers for assistance; if you are not skilled at removing your own blockers, this role will present significant challenges

L2 Support Engineer Key Responsibilities

• Combine technical human judgment and AI-driven tools to provide outstanding customer support, concentrating on intricate problems that AI cannot yet independently address

Basic Requirements

• A minimum of 3 years of total experience in a technical customer support position
• Foundational coding ability for troubleshooting and bug resolution purposes
• Troubleshooting Skills: Simplifying complex technical matters, exhibiting deep problem comprehension, suggesting appropriate diagnostic approaches, offering multiple resolution options, and maintaining rigorous attention to detail
• Must be located in a North or South American time zone

About Alpha

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 for more details on this topic.

Crossover Job Code: LJ-5729-CA-Ottawa-L2SupportEngin.001