Gmail & Google Calendar AI Assistant Evaluator

IMPORTANT: after you apply please check your email. We send you a link to complete your application it is not considered until that last step is done. If you do not see it check your spam folder.

This is a fully remote position open to candidates based in United States.

Pay: $15$30/hr

Role Title: Gmail & Google Calendar AI Assistant Evaluator

Role Type: Contractor Remote

Location: United States only

We are engaging Gmail & Google Calendar AI Assistant Evaluators to collaborate on a customer-driven project enhancing AI assistant quality through real-world task this role youll 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:

1. Complete realistic everyday digital tasks (emailing scheduling booking coordinating) using AI assistant tools under standardized repeatable conditions.
2. Give an AI assistant clear instructions for real-world tasks then carefully review and verify its work for accuracy and completeness.
3. Apply detailed grading guidelines to evaluate rank and annotate assistant responses providing structured feedback that improves model performance.
4. Test scenarios involving email threads calendar invites online bookings and multi-person coordination ensuring coverage of diverse situations and edge cases.
5. Utilize AI training tools and platforms to record findings and submit evaluation data in alignment with project standards and milestones.
6. Collaborate with project trainers and contributors to resolve ambiguities refine guidelines and ensure evaluation consistency across the team.
7. Participate in ongoing quality reviews incorporating feedback to maintain rigorous evaluation standards.

Required Skills and Qualifications:

1. Are based in the US have an iPhone with iMessage and have a Facebook or Instagram account.
2. Daily hands-on use of Gmail and Google Calendar to run your own life: sending emails accepting invites scheduling and rearranging plans.
3. Regular experience coordinating with others over email or text setting up meetups following up on threads or confirming shared plans and payments.
4. Comfort booking things online independently such as restaurants appointments travel or deliveries.
5. Experience using AI tools for real practical tasks with comfort giving an AI assistant instructions and checking its work.
6. Exceptional attention to detail and accuracy when reviewing AI-generated output.
7. Strong written communication skills for clear reporting and timely updates on progress and challenges.
8. Demonstrated time management and self-organization for independent remote project participation.

Preferred Qualifications:

1. Prior experience with AI evaluation data labeling user testing or similar feedback-driven projects.
2. Familiarity with prompt writing and a practical understanding of AI assistant behaviors and limitations.
3. Experience grading or reviewing AI outputs for accuracy helpfulness and safety.

How to apply

Apply here with your profile. We will then email you a link to complete your application on the hiring platform your application is only considered once that final step is done.