AI Response Labeler / Annotator – Italian Specialty

About the Role

We’re looking for an AI Response Labeler / Annotator with deep expertise in Italian and the cultural context of Italy.

This is an AI annotation and evaluation role, not a translation or traditional localization position. Italian expertise is an essential specialization, but it represents only one component of the work. You’ll evaluate AI-generated responses across a broad range of topics, tasks, and real-world scenarios. Much of the content, annotation guidance, and day-to-day work will be in English.

You’ll perform side-by-side comparisons of responses generated by different AI models and determine which response better meets the user’s needs. This requires strong analytical judgment, the ability to interpret detailed guidelines, and the consistency to apply those standards across a high volume of evaluations.

Successful candidates will be comfortable assessing content beyond language quality alone. You may be asked to evaluate factual accuracy, relevance, completeness, reasoning, instruction-following, clarity, safety, tone, and overall usefulness.

What You'll Do

• Perform side-by-side comparisons of AI-generated responses and determine which response is stronger.
• Evaluate responses for factual accuracy, relevance, completeness, clarity, reasoning, instruction-following, tone, and overall quality.
• Assess content written in English, Italian, or a combination of both, depending on the assigned scenario.
• Evaluate a broad range of content, including general-purpose questions and answers, web-search results, file-based tasks, image-based responses, content-generation requests, and single-turn and multi-turn conversations.
• Apply Italian expertise when evaluating language, terminology, tone, regional conventions, idioms, and cultural context specific to Italy.
• Evaluate the complete quality of a response rather than focusing only on grammar, translation, or language fluency.
• Identify subtle but meaningful differences between responses, including unsupported claims, incomplete reasoning, missed instructions, unnatural phrasing, cultural inaccuracies, and differences in usefulness.
• Apply detailed, scenario-specific annotation guidelines accurately and consistently.
• Make independent evaluation decisions when examples or guidelines don’t provide an obvious answer.
• Document decisions clearly and provide concise, evidence-based rationale when required.
• Complete evaluations within established time and productivity expectations without sacrificing accuracy.
• Maintain consistent judgment across a high volume of varied assignments.
• Participate in training, guided practice, calibration sessions, qualification reviews, and ongoing quality-review activities.
• Incorporate feedback and adjust evaluation decisions to remain aligned with team and client quality standards.

What You'll Bring

• Native-level or professional fluency in Italian.
• Deep familiarity with the linguistic conventions, regional vocabulary, idioms, tone, and cultural context of Italian as used in Italy.
• Strong English fluency and reading comprehension, including the ability to understand complex prompts, AI-generated responses, and detailed annotation guidelines written in English.
• Strong general analytical and critical-thinking skills that extend beyond language evaluation.
• Ability to evaluate content across varied topics, formats, and task types.
• Ability to assess factuality, relevance, reasoning, clarity, instruction-following, cultural appropriateness, and overall usefulness.
• Ability to recognize subtle differences in meaning, quality, tone, and user intent.
• Sound judgment when applying structured evaluation criteria to ambiguous or unfamiliar scenarios.
• Strong written communication skills and the ability to explain evaluation decisions clearly and concisely.
• Excellent attention to detail and the ability to maintain accuracy while working within established time expectations.
• Ability to learn and consistently apply detailed evaluation frameworks.
• Ability to work independently while remaining aligned with shared quality standards.
• Comfort performing repetitive, detail-oriented work for extended periods while maintaining focus, accuracy and consistent judgement. 
• Ability to receive feedback, recalibrate decisions, and adapt as evaluation guidelines evolve.

Preferred Qualifications

• Experience performing side-by-side labeling, annotation, comparative content evaluation, or quality assessment.
• Experience evaluating AI-generated responses or contributing to model-quality assessment.
• Experience with data labeling or annotation.
• Experience evaluating search relevance, content quality, factual accuracy, or user-facing digital experiences.
• Experience working with detailed guidelines, rubrics, or structured decision-making frameworks.

Work Pace and Productivity Expectations

This is a highly structured and repetitive role that involves completing similar evaluation tasks throughout the workday. Candidates should be comfortable maintaining focus, accuracy, and consistent judgment while reviewing a high volume of AI-generated content.

Most evaluation tasks are expected to take approximately 15 minutes, and employees are generally expected to complete a minimum of 25 tasks per day. Some tasks may take more or less time depending on their complexity.

Success in this role requires balancing productivity with quality. Employees must meet established daily expectations while carefully applying annotation guidelines and providing accurate, well-supported evaluation decisions.

Training and Qualification

All new hires must successfully complete a structured onboarding and qualification program before beginning production work.

The program includes training sessions, guided practice exercises, calibration against established quality benchmarks, and a formal qualification review.

Training is intended to establish consistent evaluation judgment across the team. Language fluency alone will not be sufficient to qualify. Employees must also demonstrate the ability to evaluate broader response quality, follow detailed annotation guidelines, explain their decisions, and complete work within the expected timeframe.

Employees will continue to receive feedback, quality reviews, and calibration support after entering production.

Compensation

We offer competitive compensation aligned with local market conditions and experience.

The estimated compensation range is CLP 13,333–15,555 per hour. The estimated full-time monthly equivalent is CLP 2,311,100–2,696,300 per month.

Actual compensation will be determined based on experience, skills, and internal equity.

Location and Employment Structure

Chile

This role will be hired through an Employer of Record partner to support compliance with local employment, payroll, and benefits requirements. Eligible employees will receive benefits in accordance with local requirements and the terms of their employment.

During the approximately 30-day training and qualification period, employees must work from 9:00 a.m. to 5:00 p.m. Pacific Time. After successfully completing training, employees may work standard business hours within their local time zone.