Gmail & Google Calendar AI Assistant Evaluator (Remote AI Evaluation Contract)

Join Jobtacular as a remote Gmail & Google Calendar AI Assistant Evaluator (Remote AI Evaluation Contract) ($15 - $30/hour). We partner with leading AI research laboratories across major English-speaking markets to evaluate complex responses, design realistic domain scenarios, and calibrate next-generation foundation models using deep professional expertise in Gmail, Google Calendar, AI Usage, Scheduling.

What You Will Do

• Give an AI assistant clear instructions for real-world tasks, then carefully review and verify its work for accuracy and completeness.
• Apply detailed grading guidelines to evaluate, rank, and annotate assistant responses, providing structured feedback that improves model performance.
• Test scenarios involving email threads, calendar invites, online bookings, and multi-person coordination, ensuring coverage of diverse situations and edge cases.
• Utilize AI training tools and platforms to record findings and submit evaluation data in alignment with project standards and milestones.
• Collaborate with project trainers and contributors to resolve ambiguities, refine guidelines, and ensure evaluation consistency across the team.
• Participate in ongoing quality reviews, incorporating feedback to maintain rigorous evaluation standards.
• Are based in the US, have an iPhone with iMessage, and have a Facebook or Instagram account.

Who We Are Looking For

• Strong written communication skills for clear reporting and timely updates on progress and challenges.
• Demonstrated time management and self-organization for independent, remote project participation.
• Prior experience with AI evaluation, data labeling, user testing, or similar feedback-driven projects.
• Working knowledge of prompt writing and a practical understanding of AI assistant behaviors and limitations.
• Experience grading or reviewing AI outputs for accuracy, helpfulness, and safety.
• Compensation Band: $15 - $30/hour
• Work Location: Remote (100% Remote / Asynchronous Flexibility)

Compensation & Remote Structure

• Compensation Rate: $15 - $30/hour (contract specialist remuneration)
• Work Arrangement: 100% Remote / Work From Home
• Eligible Remote Countries: United States, United Kingdom, Canada, Australia, New Zealand, Ireland, and South Africa
• Core Competencies: Gmail, Google Calendar, AI Usage, Scheduling, Emails, Google Meetings
• Hiring Agency: Jobtacular

Direct Application Process: Click the Apply button on this page to proceed directly to our partner application portal and submit your profile for immediate consideration.