Hospitality Worker (Toast POS User) (Remote AI Evaluation Contract)

Welcome to Jobtacular! We connect top-tier domain practitioners directly with frontier AI labs. We are on the hunt for a sharp, detail-oriented Hospitality Worker (Toast POS User) (Remote AI Evaluation Contract) ($28 - $92/hour) to assist with benchmarking and human evaluation. If you have deep experience in Toast POS, Restaurant Operations, Point of Sale (POS) Systems, Order & Payment Management, this flexible engagement gives you the freedom to set your own hours while earning top-market hourly rates.

The Role & What You'll Tackle

the partner network is engaging hospitality workers to contribute to a customer initiative related to restaurant technology. In this role, you'll apply your expertise to help train next-generation AI systems. Your work will shape how models learn, reason, and perform through high-quality, real-world input. No prior experience in AI is required — your domain knowledge is what matters.

The Role & What You'll Tackle

1. Analyze and provide feedback on Toast POS workflows, including order entry, payment processing, and reporting features.
2. Create scenario-based documentation and step-by-step guides reflecting real restaurant operations using Toast POS.
3. Deliver comprehensive reviews of system functionalities, identifying opportunities for improvement and troubleshooting common pain points.
4. Contribute detailed explanations of best practices for implementing, configuring, and optimizing Toast POS in a variety of restaurant settings.
5. Annotate and evaluate authentic transaction data, menus, and order flows to enhance AI understanding of restaurant POS operations.
6. Facilitate knowledge transfer by clearly articulating Toast POS concepts through both written and verbal communication.
7. Participate in collaborative sessions to refine prompts, tasks, or datasets related to Toast POS and restaurant order management.

Your Background & Core Strengths

1. Currently employed in hospitality, using Toast POS in daily operations.
2. Deep understanding of operational workflows and how point of sale systems interface with order and payment processes.
3. Exceptional written and verbal communication skills, with a focus on clarity and accuracy.
4. Proven ability to document processes and provide user-friendly explanations for technical and non-technical audiences.
5. Familiarity with various restaurant concepts (quick service, casual, fine dining) and how POS requirements differ among them.
6. Experience training, mentoring, or supporting others in adopting new restaurant technology solutions is a plus.

Rate, Schedule & Why You'll Love It

This contract position is offered at $28 - $92/hour with immediate onboarding upon approval. Work 100% remotely from the United States, UK, Canada, Australia, New Zealand, or Ireland. Candidates are evaluated on verified subject matter mastery. Select Apply Now below to access the official candidate assessment portal directly.