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Jacob Q.

Jacob Q.

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Freelancer Overview

Jacob Quaife AI Annotation Specialist • Prompt Engineer • AI Content Creator Phoenix, AZ • [email protected] • (602) 338-0301 • linkedin.com/in/jacob-quaife-2025b3101 PROFESSIONAL SUMMARY AI annotator and independent creative technologist with hands-on experience evaluating large language model outputs across reasoning, instruction-following, and creative generation tasks. Self-taught in AI tooling and application development — built and shipped AI-powered products using the Anthropic Claude API, including adaptive interactive systems and generative content pipelines. Combines deep familiarity with model behavior and prompt engineering with a background in creative writing and media production. Brings genuine enthusiasm for the work and a practitioner's instinct for where models succeed and fail. EXPERIENCE Generalist AI Annotator • Outlier.ai Oct 2025 – Present – Evaluate and rank LLM outputs for quality across diverse task categories including creative writing, reasoning, instruction-following, and factual accuracy – Provide detailed, calibrated feedback on model responses to support RLHF and fine-tuning workflows – Maintain consistent annotation standards across high-volume tasks with varied prompt complexity – Apply nuanced judgment to edge cases, ambiguous prompts, and multi-step reasoning chains Independent AI Developer & Creative Technologist • 32nd St Productions 2024 – Present – Built ORACLE — an AI-powered adaptive escape room using the Anthropic Claude API with be