Senior Technical Support Analyst at Crossover

Educational support organizations face mounting complexity at a time when 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 remain constrained by disconnected tools, manual handoffs, and fragile workflows that break down under pressure.

Our approach bridges this divide through a distinctly different architecture: AI-enhanced "cyborg" agents embedded within a functioning educational environment. In this position, you will influence how the entire system evolves. Each resolution refines future automation capabilities, each root cause investigation drives process and policy decisions, and each complex scenario you solve scales benefits across thousands of students and educators.

This position requires production-grade, hands-on problem resolution within a service context. You will diagnose unclear, multi-party failures spanning learning software, SIS platforms, identity infrastructure, network environments, and operational procedures; use AI to generate hypotheses, validate theories, and speed resolution timelines; capture the human logic that trains both systems and colleagues; and surface patterns that convert isolated fixes into sustainable, organization-wide enhancements.

This is not about ticket sorting, script execution, or "escalate and move on." If you excel when documentation is sparse, when issues cross engineering, operations, and pedagogy, and when you can shift between technical troubleshooting and stakeholder communication without sacrificing precision, this role will suit you well.

What You Will Be Doing

• AI-Augmented Customer Resolutions: Investigate complex escalations flagged by AI systems, contribute human judgment where AI capabilities fall short, and subsequently enhance the AI system to narrow that gap

What You Won’t Be Doing

• Spending two full months ramping up; you will be expected to gain proficiency on several products within your first month (we recognize this timeline is demanding)
• Depending on your managers for help; if you are not skilled at removing your own blockers, you will find this role challenging

Senior Technical Support Analyst Key Responsibilities

• Combine technical human judgment with AI capabilities to provide outstanding customer support, concentrating on challenging cases that AI cannot yet independently resolve

Basic Requirements

• A minimum of 3 years total experience in a technical customer support position
• Foundational coding skills sufficient for troubleshooting and bug correction
• Troubleshooting Skills: Communicating complex issues in accessible language, exhibiting deep problem comprehension, suggesting appropriate troubleshooting approaches, offering multiple resolution pathways, and maintaining strong 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 www.crossover.com/help-and-faqs for more details on this topic.

Crossover Job Code: LJ-5729-CA-Calgary-SeniorTechnica