Customer Support Engineer, Alpha (Remote) - $60,000/year USD

Company: Crossover

A student attempts to begin a lesson and the application fails to load. A guide's dashboard displays incorrect mastery scores. L1 support and the AI assistant have both attempted resolution without success. The issue now belongs to you — and a child's educational progress depends on your ability to identify what has gone wrong.
The majority of your time is spent resolving tickets that have defeated other tiers of support, spanning the multiple 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 diagnosis, then validate all output it produces, because an incorrect solution delivered to a classroom scales its damage rapidly. You will acquire working knowledge of a new product nearly every week. This is the core function, not a cautionary note.
You take ownership of each issue from start to finish: replicate the problem, identify its root cause, and resolve it in the minimum number of interactions required to restore functionality for the student or guide. The diagnostic reasoning you document improves the capabilities of the next agent and the next AI workflow, ensuring your solution delivers value well beyond the current ticket. With experience, you become the escalation point 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 support tickets from students, parents, and guides that neither AI nor L1 support successfully closed.
* Replicate failures in environments that match the user's device, application version, and configuration, utilizing logs and actual artifacts.
* Conduct investigation across Alpha's suite of learning applications (ticketing systems, Slack channels, knowledge repositories, logs) prior to escalation.
* Deploy AI tools (such as ChatGPT or Claude) to accelerate diagnosis, anchor them in verified documentation, and validate all generated output.
* 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.
* Record your diagnostic reasoning so subsequent agents, and future AI workflows, can leverage it.
What You Won’t Be Doing
* Operating from scripts or decision trees designed for a single product.
* Working the simple ticket queue. AI already resolves tickets that require only knowledge-base lookups.
* Escalating challenging problems to engineering without first replicating and narrowing the scope.
* Allowing AI to perform reasoning on your behalf, or submitting its output without verification.
* Waiting for direction, or depending on others to remove obstacles.
Customer Support Engineer Key Responsibilities
Diagnose and resolve complex, ambiguous customer issues to root cause across Alpha's suite of 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 constructing and reading REST API calls and JSON, interpreting HTTP status codes (such as 401 vs 404 and 429 vs 403), and operating 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-AR-BuenosAi-CustomerSuppor.001

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