A student attempts to begin a lesson, but the application fails to load. A guide's interface displays incorrect mastery data. Both L1 support and the AI have already attempted resolution without success. The issue now falls to you — and a child's educational session depends on your ability to identify the underlying cause.

The majority of your time will be spent on tickets that others were unable to resolve, spanning the multiple applications that comprise Alpha's learning platform. You will replicate the issue in an environment matching the student's or guide's configuration, analyze logs and documentation, leverage AI to accelerate your workflow, then validate all outputs — because an incorrect solution deployed in a classroom setting escalates rapidly. Ramping up on a new product nearly every week is standard.

This is the core of the role, not an exception.

You assume full ownership of each issue: replicate it, identify the root cause, and resolve it with the minimum number of interactions necessary to restore functionality for the student or guide. The diagnostic reasoning you document strengthens both the next support agent and future AI workflows, ensuring your solution continues to deliver value well beyond the current ticket. As you progress, you will become the escalation point for the team's most challenging education-product issues.

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

What You Will Be Doing

• Resolve complex, escalated support tickets from students, parents, and guides that neither AI nor L1 support could successfully close.
• Replicate issues in an environment that accurately reflects the user's device, application version, and configuration, using logs and actual user artifacts.
• Conduct thorough investigation across Alpha's learning applications (ticketing systems, Slack channels, knowledge repositories, logs) prior to escalation.
• Utilize AI tools (including ChatGPT or Claude) to accelerate diagnostic work, anchor them in verified documentation, and validate all generated 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 genuine product defect is identified.
• Create detailed documentation of your diagnostic process so subsequent agents and AI workflows can leverage it.

What You Won’t Be Doing

• Working from scripts or decision trees for a single product.
• Processing the simple ticket queue. AI already resolves issues that require only knowledge-base lookups.
• Escalating difficult problems to engineering without first replicating and narrowing the scope.
• Allowing AI to perform reasoning on your behalf, or forwarding its output without verification.
• Waiting for direction or for others to remove blockers from your path.

Escalation Engineer Key Responsibilities

Diagnose and resolve complex, ambiguous customer issues to root cause across Alpha's suite of education products.

Basic Requirements

• 2+ years of hands-on technical experience in roles such as technical support, software engineering, QA, system administration, or DevOps. The specific job title need not be "support."
• Proficient in making and interpreting REST API calls and JSON, understanding HTTP status codes (such as 401 vs 404 and 429 vs 403), and working within command-line environments and log files.
• Practical experience incorporating AI tools (such as ChatGPT or Claude) into your daily technical workflows.
• Professional-level fluency in written and spoken English.
• Available to work a full 40-hour week during US business hours (Eastern Time). This position operates on a full US-daytime schedule.
• Located in North America, Central America, South America, Australia, New Zealand, the United Kingdom, Ireland, or the Philippines.

Nice-to-have Requirements

• Background supporting non-technical end users (within education, edtech, or consumer applications), rather than solely IT professionals.
• Demonstrated experience directing AI tools and identifying their errors.
• Proven ability troubleshooting across multiple unrelated products, not limited to a single platform.
• Developer-level technical depth: capable of reading code or tracing an API call when the situation requires 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-Manila-EscalationEngi