Gmail & Google Calendar AI Assistant Evaluator

Test AI assistants on realistic email, scheduling, booking, and coordination tasks. Give clear instructions, check results, and record whether the assistant completed each task accurately and completely.

You will:

- Complete practical tasks involving Gmail, Google Calendar, email threads, invitations, bookings, and multi-person coordination.

- Check AI assistant work for accuracy, completeness, helpfulness, and reliability.

- Grade, rank, and annotate responses using evaluation guidelines.

- Record findings and help maintain consistent evaluation quality.

What you need:

- Regular hands-on experience with Gmail and Google Calendar for scheduling, invitations, rearranging plans, and coordination.

- Independent experience booking restaurants, appointments, travel, deliveries, or similar services online.

- An iPhone with iMessage and an active Facebook or Instagram account.

- Strong written communication, attention to detail, organization, and self-management.

- Comfort instructing AI tools and checking their work.

- Previous AI evaluation, data labeling, user testing, prompt writing, or AI feedback experience is helpful but not required.

OpenTrain welcomes applicants based on relevant skills and experience. This is a remote role for candidates in the United States who are fluent in English.