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Educational support systems are collapsing under growing complexity as demands from students, families, and institutions intensify. Modern schools require immediate, AI-powered responses spanning learning platforms, student information systems, hardware, and operational processes. Yet most support organizations remain trapped in disconnected tools, manual handoffs, and fragile workflows that crumble when tested by real-world conditions. We address this challenge through a radically different approach: AI-enhanced "cyborg" support personnel positioned at the heart of a dynamic educational environment. In this position, you will influence how the platform evolves. Each resolution you deliver refines future automation capabilities, each root cause investigation shapes process design and governance, and each complex scenario you resolve creates better outcomes for thousands of learners and teaching professionals. This is direct, production-level troubleshooting within a live service context. You will investigate unclear, multi-party breakdowns spanning educational software, student information platforms, authentication infrastructure, network architecture, and operational systems; use AI tools to generate hypotheses, validate theories, and speed up resolution workflows; capture the human analysis that educates both technology and personnel; and surface recurring issues that convert isolated fixes into lasting, organization-wide enhancements. This is not helpdesk queue management, checklist execution, or "forward and forget." If you excel when documentation is missing, when challenges cross engineering, operations, and pedagogy, and when you can transition from technical diagnosis to stakeholder communication while maintaining precision, this position will suit you well. What You Will Be Doing AI-Enhanced Customer Resolution: Evaluate escalated complex cases forwarded by AI platforms, contribute human judgment where AI capabilities are insufficient, and subsequently enhance the AI system to narrow that performance gap What You Won’t Be Doing Spending two full months onboarding; you will need to achieve proficiency across multiple products within your first month (we acknowledge this expectation is demanding) Depending on managers to remove obstacles; if you cannot independently overcome blockers, you will find this role challenging Technical Support Engineer Key Responsibilities Combine technical human judgment with AI tooling to provide outstanding customer support, concentrating on sophisticated problems that AI systems cannot yet independently address Basic Requirements Minimum of 3 years total experience in a technical customer support position Foundational programming ability for troubleshooting and bug resolution purposes Troubleshooting Capabilities: Translating complicated problems into accessible language, exhibiting deep problem comprehension, suggesting appropriate diagnostic approaches, offering multiple resolution options, and maintaining rigorous attention to detail Must be located in a North or South American time zone 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-BR-PortoAle-TechnicalSuppo1.001