Technical Support Specialist, Alpha (Remote) - , USD

Educational support organizations face mounting complexity as schools, students, and families demand more responsive service. Today's schools require immediate, AI-powered assistance spanning learning platforms, student information systems, hardware devices, and operational workflows. Yet most support teams rely on disconnected tools, manual handoffs, and fragile processes that break down under pressure.

We address this challenge through a different approach: AI-enhanced "cyborg" agents working at the heart of a dynamic educational environment. In this position, you will influence how the system evolves. Each resolution you deliver feeds future automation, each root cause investigation shapes process and policy, and each edge case you solve scales benefits to thousands of students and educators.

This is direct, production-level problem solving within a service context. You will investigate unclear, multi-party failures spanning learning applications, student information systems, identity management, network infrastructure, and operational processes; use AI to generate hypotheses, validate approaches, and speed up resolutions; capture the human logic that trains both systems and colleagues; and surface patterns that convert isolated fixes into lasting, organization-wide enhancements.

This is not routine ticket sorting, procedure adherence, or "forward and wait." If you excel when documentation is sparse, when challenges touch engineering, operations, and pedagogy, and when you can shift between technical analysis and stakeholder communication without compromising precision, this role will suit you well.

What You Will Be Doing

• AI-Augmented Customer Resolutions: Examine escalated tickets flagged by AI systems, apply human judgment to scenarios where AI capabilities are insufficient, and refine the AI system to close those gaps

What You Won’t Be Doing

• Spending two full months on onboarding; you will be expected to gain proficiency across multiple products within the first month (we recognize this is demanding)
• Depending on managers for unblocking; if you are not skilled at removing your own obstacles, this role will likely be challenging

Technical Support Specialist Key Responsibilities

• Combine human technical expertise with AI tools to provide outstanding customer support, concentrating on intricate problems that AI cannot yet handle independently

Basic Requirements

• 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

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.

Crossover Job Code: LJ-5729-CA-Toronto-TechnicalSuppo.002