Technical Support Engineer, Alpha (Remote) - $60,000/year USD - #228974

Educational support organizations face mounting complexity as schools, students, and families demand faster, more intelligent responses across learning platforms, student information systems, devices, and operational workflows. Most teams remain constrained by disconnected tools, manual handoffs, and fragile processes that break down under real-world pressure.

We address this challenge through a distinct approach: AI-enhanced "cyborg" agents embedded within a dynamic educational environment. In this position, you will influence how the system evolves. Each resolution strengthens future automation, each root cause investigation shapes process and policy, and each complex scenario you solve drives better outcomes for 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, SIS platforms, identity systems, networks, and operational workflows; use AI to form hypotheses, validate theories, and speed resolution; capture the human reasoning that trains both systems and teams; and proactively surface patterns that convert isolated fixes into lasting, organization-wide improvements.

This is not basic ticket management, script execution, or passive escalation. If you excel when documentation is sparse, when issues cross engineering, operations, and academic domains, and when you can shift from technical diagnosis to stakeholder communication without compromising precision, this role will suit you well.

What You Will Be Doing

• AI-Augmented Customer Resolutions: Examine complex tickets escalated by AI systems, contribute human judgment where AI is insufficient, and then enhance the AI system to close that gap
  
  

What You Won’t Be Doing

• Spending two full months onboarding; you will be expected to ramp up on several products within the first month (we recognize this is demanding)
• Depending on your managers for assistance; if you are not skilled at self-unblocking, you will likely find this role challenging
  
  

Technical Support Engineer Key Responsibilities

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

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
• Must be based 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-TechnicalSuppo1.003