Gmail & Calendar AI Evaluator - Remote, Part-Time

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

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