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.