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Gmail & Google Calendar AI Assistant Evaluator

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Job details

Pay

$15–$30 USD/hr

Engagement

Contract, part-time

Location

Remote

United States only

Posted

Sep 26, 2026

OpenTrain on Trustpilot

The work

You will test AI assistants using everyday email, calendar, booking, scheduling, and coordination tasks. You will check whether each assistant completes the task accurately and fully, then record your findings.

The work includes giving clear instructions, grading and ranking responses, adding annotations, and submitting structured evaluation data. You may also identify unusual cases, discuss unclear examples with other contributors and trainers, and use feedback during quality reviews.

  • Complete repeatable tasks involving Gmail messages, email threads, calendar invitations, bookings, scheduling, and multi-person coordination.
  • Check AI-generated work for accuracy, completeness, and adherence to evaluation guidelines.
  • Grade, rank, and annotate assistant responses using structured AI training tools.
  • Record findings and submit evaluation data.
  • Identify edge cases and resolve unclear examples with contributors and trainers.

Requirements

This is a remote contractor role with part-time employment. Candidates must be based in the United States and fluent in English.

  • Language: Fluent in English.
  • Experience: Daily hands-on experience with Gmail and Google Calendar, including sending messages, accepting invitations, scheduling, and changing plans.
  • Coordination: Experience working with others by email or text and booking restaurants, appointments, travel, deliveries, or similar services.
  • Devices and accounts: An iPhone with iMessage and an active Facebook or Instagram account.
  • Skills: Clear written communication, careful attention to detail, time management, self-organization, and comfort instructing AI tools and checking their work.
  • Skills: Gmail, Google Calendar, AI Usage, Scheduling, Emails, Google Meetings

Open to applicants in

  • United States

Preferred

  • Helpful experience: AI evaluation, data labeling, user testing, prompt writing, or reviewing model outputs for accuracy, helpfulness, and safety.

How to apply

  1. Press Apply now. You create a free OpenTrain account and add your resume.
  2. Finish your application on the hiring company's site. The company decides who it hires, so it runs its own form. It asks for your resume again, your LinkedIn profile, your phone number, your location and answers to 8 screening questions.
  3. Take a short AI interview.

OpenTrain on Trustpilot

Job ID: cmui6fowy00000bgmk6fwt0j9

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