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

A student is ready to learn, but the app refuses to load. A guide's dashboard displays incorrect mastery scores. L1 support and the AI have already attempted resolution without success. The issue is now yours — and a child's learning day depends on you identifying what has actually gone wrong.

The majority of your workday will involve tickets that no one else managed to resolve, spanning the diverse applications that comprise Alpha's learning platform. You will replicate the issue in a setup that matches the student's or guide's environment, examine logs and documentation, leverage AI to accelerate your work, and then validate everything it produces, because an incorrect answer delivered to a classroom scales its impact rapidly. Ramping up on a new product nearly every week is expected. This is the nature of the role, not a caution.

Each problem is yours from start to finish: replicate it, identify the underlying cause, and resolve it with the fewest interactions necessary to restore the student or guide's workflow. The documentation you create strengthens the next agent and the next AI system, ensuring your solution continues to add value well beyond your current ticket. In time, you will become the go-to resource the team relies on for its most challenging education-product issues.

If you seek the difficult, unclear problem, and you genuinely care that the product ultimately helps a child learn, submit your application.

What You Will Be Doing

• Address unclear, escalated support requests from students, parents, and guides that AI and L1 could not resolve.
• Replicate issues in environments mirroring the user's device, application, and setup, using logs and actual data.
• Conduct thorough investigations across Alpha's learning applications (tickets, Slack, knowledge repositories, logs) prior to escalating.
• Use AI tools (such as ChatGPT or Claude) to accelerate diagnosis, anchor them in authentic documentation, and validate all outputs.
• Engage clearly and professionally with 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 confirmed.
• Record your diagnostic reasoning so future team members and AI workflows can leverage it.

What You Won’t Be Doing

• Working from scripts or decision trees for a single product.
• Managing the simple queue. AI already handles tickets solvable through knowledge-base searches.
• Escalating difficult problems to engineering without first replicating and isolating them.
• Allowing AI to do your thinking, or delivering its responses without verification.
• Waiting for direction, or relying on others to remove blockers.

Technical Support Specialist Key Responsibilities

Diagnose and resolve complex, ambiguous customer issues to their 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. Your job title does not have to be "support."
• Comfortable constructing and reading REST API calls and JSON, understanding HTTP status codes (such as 401 vs 404 and 429 vs 403), and operating in command line and log environments.
• Practical experience using AI tools (such as ChatGPT or Claude) in daily technical work.
• Professional fluency in written and spoken English.
• Available to work full-time (40 hours/week), with all working hours 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 applications), not only IT professionals.
• Practical experience guiding AI tools and identifying their errors.
• A proven history of troubleshooting across multiple unrelated products, not a single one.
• Developer-level proficiency: capable of reading code or tracing an API call when necessary.

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-Toronto-TechnicalSuppo.007