Posted Sep 30, 2026

Toast POS Specialist

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Role: Toast POS Specialist – AI Training & Restaurant Technology Job Type: Contractor Location: Remote Compensation: $28–$92/hour Domain: Toast POS | Restaurant Operations | Point of Sale (POS) Systems | Order & Payment Management Role Overview We are looking for experienced Toast POS Specialists to contribute to a customer initiative related to restaurant technology. The role involves applying Toast POS and restaurant operations expertise to help train next-generation AI systems through high-quality, real-world input. No prior AI experience is required. Key Responsibilities Analyze and provide feedback on Toast POS workflows, including order entry, payment processing, and reporting features. Create scenario-based documentation and step-by-step guides reflecting real restaurant operations using Toast POS. Provide detailed explanations of best practices for implementing, configuring, and optimizing Toast POS across restaurant settings. Annotate and evaluate authentic transaction data, menus, and order flows to enhance AI understanding of restaurant POS operations. Clearly communicate Toast POS concepts through written and verbal communication. Key Requirements Significant hands-on experience with Toast POS, including configuration, troubleshooting, and daily operation in restaurants. Deep understanding of restaurant operational workflows and how POS systems interface with order and payment processes. Exceptional written and verbal communication skills, with a focus on clarity and accuracy. Proven ability to document processes and provide user-friendly explanations for technical and non-technical audiences. Familiarity with various restaurant concepts, including quick service, casual, and fine dining. Application Process Submit application & screening questions. Complete a ~30-minute AI Interview. Hiring Manager Review. Selected candidates proceed to onboarding.