Remote Gmail & Google Calendar AI Assistant Evaluator | Direct-Apply Contract

RemoteWork Talent Agency has an immediate remote opening for a Remote Gmail & Google Calendar AI Assistant Evaluator | Direct-Apply Contract earning $15 - $30/hour. In this flexible work-from-home engagement (open to candidates in the US, UK, Canada, Australia, NZ, and Ireland), you will apply practical mastery of Gmail, Google Calendar, AI Usage, Scheduling to stress-test large language models, verify factual rigor, and build gold-standard evaluation datasets.

Key Duties & Project Scope

• Apply detailed grading guidelines to evaluate, rank, and annotate assistant responses, providing structured feedback that improves model performance.
• 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.

Candidate Requirements

• Demonstrated time management and self-organization for independent, remote project participation.
• 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

Pay Rate & Contract Overview

• 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: RemoteWork Talent Agency

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.