Gmail & Google Calendar AI Assistant Evaluator, Remote- Contract

Role Title

Gmail & Google Calendar AI Assistant Evaluator

Role Type

Contract, Remote

Location

United States

Required Skills

• Gmail
• Google Calendar
• AI Usage
• Scheduling
• Emails
• Google Meetings

In this role, you'll use your everyday experience managing your digital life — email, calendars, bookings, and coordination — to help train and evaluate next-generation AI assistants. Your work will shape how AI models handle the real tasks people delegate every day.

Key Responsibilities

• Complete realistic, everyday digital tasks (emailing, scheduling, booking, coordinating) using AI assistant tools under standardized, repeatable conditions.
• Give an AI assistant clear instructions for real-world tasks, then carefully review and verify its work for accuracy and completeness.
• 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.

Required Skills and Qualifications

• 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.
• Comfort booking things online independently, such as restaurants, appointments, travel, or deliveries.
• Experience using AI tools for real, practical tasks, with comfort giving an AI assistant instructions and checking its work.
• Exceptional attention to detail and accuracy when reviewing AI-generated output.
• Strong written communication skills for clear reporting and timely updates on progress and challenges.
• Demonstrated time management and self-organization for independent, remote project participation.

Preferred Qualifications

• Prior experience with AI evaluation, data labeling, user testing, or similar feedback-driven projects.
• Familiarity with prompt writing and a practical understanding of AI assistant behaviors and limitations.
• Experience grading or reviewing AI outputs for accuracy, helpfulness, and safety.