Escalation Engineer Alpha Remote - 60 000 Year USD

A student attempts to begin a lesson and the application fails to load. A guide reviews their dashboard and notices incorrect mastery scores displayed. L1 support and the AI have both attempted resolution without success. The issue now belongs to you — and a child's learning session depends on your ability to identify the underlying problem.

The majority of your time is dedicated to tickets that remain unresolved by others, spanning the various applications that comprise Alpha's learning platform. You replicate the issue in an environment matching the student's or guide's configuration, examine logs and documentation, leverage AI to accelerate your work, and then validate each output it provides, because an incorrect solution deployed to a classroom creates cascading problems. Ramping up on a new product nearly every week is standard. That is the nature of this role, not a cautionary note.

You take complete ownership of each issue: replicate it, identify the root cause, and resolve it with the minimum number of interactions required to restore functionality for the student or guide. The diagnostic reasoning you document strengthens the capability of the next agent and the next AI workflow, ensuring your resolution continues to deliver value well beyond the current ticket. In time, you become the go-to resource for the team's most challenging education-product issues.

If you are drawn to difficult, ambiguous problems, and you genuinely care that the product ultimately supports a child's education, submit your application.

What You Will Be Doing

• Resolve complex, escalated tickets from students, parents, and guides that neither AI nor L1 support were able to close.
• Replicate failures in an environment that matches the user's device, application, and configuration, utilizing logs and actual artifacts.
• Investigate across Alpha's suite of learning applications (tickets, Slack, knowledge bases, logs) prior to escalating.
• Use AI tools (such as ChatGPT or Claude) to accelerate diagnosis, anchor them in genuine documentation, and validate every result.
• Communicate with clarity and composure to non-technical users, collecting sufficient information upfront to enable single-pass resolution.
• Escalate issues to engineering with comprehensive diagnostic context when a product defect is confirmed.
• Document your diagnostic reasoning so subsequent agents and AI workflows can apply it.
  
  

What You Won’t Be Doing

• Following predetermined scripts or decision trees for a single product.
• Processing the simple queue. AI already resolves tickets that require only a knowledge-base lookup.
• Escalating difficult problems to engineering without first replicating and isolating them.
• Allowing AI to conduct analysis on your behalf, or submitting its output without verification.
• Waiting for direction, or for another party to remove blockers.
  
  

Escalation Engineer Key Responsibilities

Resolve complex, ambiguous customer issues to root cause across Alpha's education products.

Basic Requirements

• 2+ years in a hands-on technical role such as technical support, software engineering, QA, sysadmin, or DevOps. The title does not need to be "support."
• Comfortable making and reading REST API calls and JSON, interpreting HTTP status codes (such as 401 vs 404 and 429 vs 403), and working in a command line and logs.
• Hands-on experience using AI tools (such as ChatGPT or Claude) in your daily technical work.
• Professional fluency in English, written and spoken.
• Able to work a full 40-hour week during US business hours (Eastern Time). This is a full US-daytime shift.
• Based in North America, Central America, South America, Australia, New Zealand, the United Kingdom, Ireland, or the Philippines.
  
  

Nice-to-have Requirements

• Experience supporting non-technical end users (in education, edtech, or consumer apps), not just IT professionals.
• Hands-on experience directing AI tools and catching their mistakes.
• A track record of troubleshooting across several unrelated products, not just one.
• Developer-grade depth: you can read code or trace an API call when the problem demands it.
  
  

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-PH-MetroCeb-EscalationEngi.001

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