Escalation Engineer, Alpha (Remote) - $60,000/year USD - #232196

A student opens the app to begin learning, but nothing loads. A guide's dashboard displays incorrect mastery data. L1 support and the AI assistant have both attempted resolution without success. The issue is now yours — and a child's ability to learn today depends on your ability to identify what has gone wrong.

The majority of your workload consists of tickets that have resisted closure by others, spanning the diverse 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 every output it provides — because an incorrect answer delivered to a classroom scales damage rapidly. You will onboard to a new product nearly every week. This is the nature of the role, not a disclaimer.

You take full ownership of each issue: replicate it, identify 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 capabilities of the next support agent and the next AI process, ensuring your solution continues to deliver value well beyond the current ticket. In time, you will become the engineer the team relies on for the most difficult education-product challenges.

If you are motivated by complex, ambiguous problems and genuinely care that the product serves to help a child learn, submit your application.

What You Will Be Doing

• Resolve complex, escalated issues from students, parents, and guides that could not be closed by AI or L1 support.
• Replicate failures in an environment mirroring the user's device, application, and configuration, utilizing logs and actual artifacts.
• Conduct investigations across Alpha's learning applications (tickets, Slack, knowledge repositories, logs) prior to escalation.
• Deploy AI tools (such as ChatGPT or Claude) to accelerate diagnosis, anchor them in authentic documentation, and validate all outputs.
• 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 logic so subsequent agents and AI workflows can apply it.
  
  

What You Won’t Be Doing

• Executing scripts or following decision trees for a single product.
• Working the simple queue. AI already resolves tickets solvable through knowledge-base lookups.
• Escalating difficult problems to engineering without first replicating and isolating them.
• Allowing AI to perform the thinking, or submitting its output without verification.
• Waiting for direction or depending on others 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.
• Available to work full-time (40 hours/week), with all working hours falling between 1:00 PM – 10:00 PM UTC (8:00 AM – 5:00 PM US Eastern).
  
  

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

Join the team building school around student growth

Alpha reimagines the school day around faster learning, stronger mentorship, and more time for students to build real-world skills.

Roles with real student impact: Alpha hires teachers (guides), operators, admissions experts, school & curriculum leaders, and remote team members.

Education work that pays like it matters: Alpha offers six-figure roles for people ready to help build a radically better school experience.

A culture built for builders: Alpha is fast-moving, ambitious, and student focused. It’s for people who want to improve the system, not maintain it.

Alpha is where you can do the most meaningful work of your career.

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-Ottawa-EscalationEngi