Customer Support Engineer - Remote

Educational support organizations face mounting complexity while schools, students, and families demand increasingly rapid responses. Schools require immediate, AI-powered assistance spanning learning platforms, student information systems, device management, and operational workflows. Yet most teams remain trapped in siloed tools, manual handoffs, and fragile processes that buckle under production pressure.
We bridge this divide through a fundamentally reimagined approach: AI-enhanced "cyborg" agents positioned at the heart of a living educational infrastructure. In this position, you will influence how the system evolves. Each resolution strengthens future automation, each root cause investigation refines process and policy, and each edge case you decode improves outcomes for thousands of students and educators.
This is production-grade, hands-on troubleshooting within a service context. You will investigate ambiguous, multi-party failures spanning learning applications, student information systems, identity infrastructure, network layers, and operational processes; use AI to generate hypotheses, validate approaches, and accelerate resolution; capture the human reasoning that trains both systems and colleagues; and surface patterns that transform isolated fixes into sustainable, organization-wide enhancements.
This is not about ticket sorting, script execution, or "escalate and wait." If you excel when documentation is sparse, when issues cross engineering, operations, and academic domains, and when you can transition from technical diagnosis to stakeholder coordination without sacrificing precision, this role will suit you well.
What You Will Be Doing
~ AI-Augmented Customer Resolutions: Investigate complex tickets escalated from AI systems, deploy human judgment where AI capabilities fall short, and subsequently enhance the AI system by addressing those gaps

What You Won’t Be Doing
Spending two full months on onboarding; you will be expected to achieve proficiency across multiple products within the first month (we recognize this timeline is ambitious)
Depending on managers for unblocking; if you are not skilled at removing your own obstacles, you will likely find this role challenging
L2 Support Engineer Key Responsibilities
~ Combine technical human judgment with AI capabilities to provide exceptional customer support, concentrating on sophisticated issues that AI cannot yet independently resolve

Basic Requirements
Must be located in North or South America
Minimum of 3 years total experience in a technical customer support role
Fundamental coding skills for troubleshooting and bug resolution purposes
Advanced generative AI proficiency (i.e., use of multiple AI tools, ability to automate workflows and custom GPTs); if you have only used LLMs for research, learning, brainstorming, or content generation, that will be considered insufficient
Troubleshooting Skills: Translating complex issues into simple terms, demonstrating robust problem comprehension, recommending appropriate troubleshooting strategies, proposing multiple solution paths, and displaying attention to detail
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-Calgary-L2SupportEngin