Remote Gmail & Google Calendar AI Assistant Evaluator — LLM & Systems Practice

Are you a domain specialist skilled in Gmail, Google Calendar, AI Usage, Scheduling? RemoteJob Staffing is seeking a remote Remote Gmail & Google Calendar AI Assistant Evaluator — LLM & Systems Practice ($15 - $30/hour) to help train and validate frontier AI systems through structured problem authoring, rubric design, and analytical output auditing from anywhere in the US, UK, Canada, or Australia.

Day-to-Day Impact

• Test scenarios involving email threads, calendar invites, online bookings, and multi-person coordination, ensuring coverage of diverse situations and edge cases.
• Utilize AI training tools and platforms to record findings and submit evaluation data in alignment with project standards and milestones.
• Collaborate with project trainers and contributors to resolve ambiguities, refine guidelines, and ensure evaluation consistency across the team.
• Participate in ongoing quality reviews, incorporating feedback to maintain rigorous evaluation standards.
• Are based in the US, have an iPhone with iMessage, and have a Facebook or Instagram account.
• Daily, hands-on use of Gmail and Google Calendar to run your own life: sending emails, accepting invites, scheduling, and rearranging plans.
• Regular experience coordinating with others over email or text — setting up meetups, following up on threads, or confirming shared plans and payments.

Essential Background & Expertise

• Prior experience with AI evaluation, data labeling, user testing, or similar feedback-driven projects.
• Working knowledge of prompt writing and a practical understanding of AI assistant behaviors and limitations.
• Experience grading or reviewing AI outputs for accuracy, helpfulness, and safety.
• Compensation Band: $15 - $30/hour
• Work Location: Remote (100% Remote / Asynchronous Flexibility)
• Available Openings: 50 open positions
• Core Competencies: Gmail, Google Calendar, AI Usage, Scheduling, Emails, Google Meetings

Rate & Flexible Work Terms

• Compensation Rate: $15 - $30/hour (contract specialist remuneration)
• Work Arrangement: 100% Remote / Work From Home
• Eligible Remote Countries: United States, United Kingdom, Canada, Australia, New Zealand, Ireland, and South Africa
• Core Competencies: Gmail, Google Calendar, AI Usage, Scheduling, Emails, Google Meetings
• Hiring Agency: RemoteJob Staffing

Direct Application Process: Click the Apply button on this page to proceed directly to our partner application portal and submit your profile for immediate consideration.