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Open nowPosted 28 days ago

Gmail & Google Calendar AI Assistant Evaluator, Remote- Contract

xperteez231 open roles

Where
United States
Work mode
Remote
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Your applicationOpen nowGmail & Google Calendar AI Assistant Evaluator, Remote- Contractxperteez · United States

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The clock on this job

Early applications get read.

12.1% of postings close within 7 days. Measured by our own scanner across the market.

Share of postings closed within
  1. 2.1%1 day
  2. 4.5%3 days
  3. 12.1%7 days
  4. 19.1%14 days
  5. 35.6%30 days
  6. 52.7%60 days
This job: posted 28 days ago

The posting

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.
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