Technical Support Specialist, Alpha (Remote) - $60,000/year USD

Company: Crossover

A student attempts to begin a lesson, but the app fails to load. A guide's dashboard displays incorrect mastery scores. L1 support and the AI have both attempted resolution without success. The issue is now yours to solve — and a child's learning session depends on you determining what has actually gone wrong.
The majority of your workday will focus on tickets that no one else has been able to resolve, spanning the various applications that comprise Alpha's learning platform. You will replicate the failure in an environment matching the student's or guide's configuration, examine logs and documentation, leverage AI to accelerate your work, and then validate everything it produces, because an incorrect response delivered to a classroom can escalate rapidly. Ramping up on a new product nearly every week is expected. This is the nature of the role, not a cautionary note.
You take full ownership of each issue: replicate it, identify the underlying cause, and resolve it with minimal back-and-forth to restore the student or guide's workflow. The diagnostic reasoning you document enables the next agent and subsequent AI workflows to operate more intelligently, ensuring your solution continues to deliver value well beyond the current ticket. As you progress, you will become the go-to resource for the team's most challenging education-product issues.
If you are drawn to complex, ambiguous problems, and you genuinely care that the product ultimately supports a child's education, you should apply.
What You Will Be Doing
* Resolve complex, escalated tickets from students, parents, and guides that both AI and L1 support were unable to close.
* Replicate failures in an environment that matches the user's device, application, and configuration, utilizing logs and actual artifacts.
* Conduct investigations across Alpha's learning applications (tickets, Slack, knowledge bases, logs) prior to escalation.
* Use AI tools (such as ChatGPT or Claude) to accelerate diagnosis, anchor them in authentic documentation, and verify all output.
* Communicate with clarity and composure to non-technical users, collecting sufficient information upfront to enable single-touch 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
* Using scripts or decision trees for a single product.
* Working the simple queue. AI already resolves tickets that can be answered with a knowledge-base reference.
* Escalating difficult problems to engineering without first replicating and isolating them.
* Allowing AI to do your thinking, or inserting its output without validation.
* Waiting for direction, or for others to remove obstacles on your behalf.
Technical Support Specialist 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-CO-COUNTRY-TechnicalSuppo.005

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