Remote: Gmail & Calendar AI Evaluator

Dover; Northern (KY); Hybrid; USD 45,000 - 60,000; Full time

Job summary

Dover is seeking a Gmail & Google Calendar AI Assistant Evaluator for a remote contract role in the United States. You will perform everyday digital tasks and guide an AI assistant to complete them, then assess and provide feedback on the results.

You will review AI outputs for accuracy, work with project trainers to refine guidelines, and participate in ongoing quality checks to ensure evaluation consistency across the team.

Qualifications

• Based in the US with reliable remote work setup.
• Daily use of Gmail and Google Calendar for personal and professional planning.
• Experience applying AI tools to real tasks and providing clear instructions.

Responsibilities

• Complete realistic, everyday digital tasks (emailing, scheduling, booking, coordinating) using AI assistant tools under standardized conditions.
• Provide clear instructions to AI assistants for real-world tasks and review their outputs for accuracy and completeness.
• Apply grading guidelines to evaluate, rank, and annotate assistant responses to improve model performance.
• Test scenarios with email threads, calendar invites, online bookings, and multi-person coordination.

Skills

Gmail

Google Calendar

AI Usage

Scheduling

Emails

Google Meetings

Job description

Dover is seeking a Gmail & Google Calendar AI Assistant Evaluator for a remote contract role in the United States. You will perform everyday digital tasks and guide an AI assistant to complete them, then assess and provide feedback on the results.

You will review AI outputs for accuracy, work with project trainers to refine guidelines, and participate in ongoing quality checks to ensure evaluation consistency across the team.