Technical Support Specialist, Alpha; Remote

Educational support infrastructures face mounting complexity as demands from students, families, and institutions accelerate. Institutions now require immediate, AI‑powered responses spanning learning management systems, student information systems, hardware, and operational processes. Yet most providers remain trapped in disconnected tools, manual handoffs, and fragile workflows that collapse when stress‑tested.

We bridge this divide through a radically different approach: AI‑enhanced "cyborg" specialists positioned at the heart of a dynamic educational environment. In this position, you will influence how the platform evolves. Each resolution refines future automation, each root‑cause investigation drives process refinement, and each edge case you decode enhances outcomes for thousands of learners and instructors. This is direct, production‑level troubleshooting within a service context.

You will diagnose unclear, multi‑party breakdowns across educational applications, student information platforms, authentication systems, network infrastructure, and operational procedures; apply AI to form hypotheses, validate, and expedite resolution strategies; capture the human logic that educates both technology and colleagues; and systematically surface patterns that transform isolated fixes into lasting, organization‑wide enhancements. This is not first‑line sorting, checklist execution, or "forward and monitor."

If you excel when documentation is sparse, when issues bridge technical teams, operations, and pedagogy, and when you can shift from system diagnostics to stakeholder coordination without sacrificing precision, this role will align with your strengths.

• Investigate escalated cases flagged by AI platforms, deploy human judgment where AI capabilities are insufficient, then refine the AI framework to reduce future gaps.

• Spending two full months onboarding; you will be required to become proficient with multiple products in the first month (we recognize this timeline is demanding).
• Depending on management for direction; if you do not excel at self‑unblocking, this role will present significant challenges.

• Combine technical human judgment with AI‑driven tools to provide superior customer support, concentrating on intricate problems that AI systems cannot independently address.

• Must be based in North or South America.
• At least 3 total years of experience in a technical customer support role.
• Basic coding skills for the purpose of troubleshooting/bug fixes.
• Troubleshooting skills:
  Explaining complex issues in simple terms, demonstrating strong problem understanding, recommending relevant troubleshooting strategies, proposing multiple solution paths, and showing attention to detail.

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.

We look forward to meeting you!

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  for more details on this topic.