Gmail and Google Calendar AI Assistant Evaluator

OpenTrain AI, Inc.; Northern (KY); Hybrid; USD 21,000 - 41,000; Part time

Job summary

OpenTrain AI, Inc. seeks a remote, part-time contractor to evaluate how AI assistants handle everyday digital tasks involving email, calendars, bookings, and coordination. You will provide instructions, verify results, and deliver structured feedback on task accuracy and completeness.

You will complete Gmail/Google Calendar tasks, test invitations and bookings, and record findings in our training tools. Strong attention to detail, excellent written communication, and self-management are

Qualifications

• Entry level role requiring strong hands-on experience with Gmail, Google Calendar, and online scheduling.
• Experience booking restaurants, appointments, travel, or similar services online.
• Must use Gmail/Google Calendar daily and coordinate with others.
• Must have an iPhone with iMessage and an active Facebook or Instagram account.
• Excellent written communication, organization, and self-management for remote work.
• Prior AI evaluation or data labeling experience is helpful but not required.

Responsibilities

• Test Gmail and Calendar tasks under consistent conditions; provide instructions.
• Check results and give structured feedback on accuracy and completeness.
• Grade, rank, and annotate assistant responses using evaluation guidelines.
• Test scenarios, record findings in training tools, and participate in quality reviews.
• Collaborate with others to resolve unclear evaluation cases.

Skills

Attention to detail

Written communication

Organization

Self-management

Remote work experience

Tools

Gmail

Google Calendar

Online bookings

Scheduling

Job description

The Work

You will test how AI assistants handle everyday digital tasks involving email, calendars, bookings, and coordination. You will provide instructions, check the results, and give structured feedback on whether the assistant completed each task accurately and completely.

• Complete realistic Gmail and Google Calendar tasks under consistent conditions.
• Test email threads, calendar invitations, online bookings, scheduling changes, and multi-person coordination.
• Grade, rank, and annotate assistant responses using detailed evaluation guidelines.
• Test different scenarios and edge cases, then record findings in the required training tools and platforms.
• Help resolve unclear evaluation cases with other contributors and take part in quality reviews.

What It Pays and Takes

This is a remote, part-time contractor role for people located in the United States. The work is listed as entry level, but you need strong hands-on experience with Gmail, Google Calendar, online bookings, and practical scheduling.

• Pay: $15-$30 per hour.
• Time: 20 or more hours per week.
• Location: United States only.
• Language: English.
• Use Gmail and Google Calendar daily for tasks such as sending emails, managing invitations, changing plans, and coordinating with others.
• Have independent experience booking restaurants, appointments, travel, deliveries, or similar services online.
• Have an iPhone with iMessage and an active Facebook or Instagram account.
• Be comfortable instructing AI tools and checking their work on real-world tasks.
• Bring exceptional attention to detail, strong written communication, organization, and self-management for remote project work.
• Previous AI evaluation, data labeling, user testing, prompt writing, or AI feedback work is helpful but not required.

About AI Training Work

AI training work uses human examples and reviews to improve how artificial intelligence systems respond. Evaluators are paid for careful judgment because their feedback helps make AI assistants more accurate, complete, and reliable.