Hollie Estrella

International humanitarian, operations, and AI data professional with experience leading nonprofit fundraising teams, supporting immigration and asylum services, training and evaluating large language models (LLMs), business ownership, and freelance engagement and brand growth strategy. Skilled in analytical thinking, empathy, strategic planning, quality evaluation, storytelling, and cross-cultural communication.

AI Data Annotator & LLM Trainer - DataAnnotation

• Train and evaluate large language models (LLMs) through structured data annotation, response evaluation, and quality review.
• Analyze AI-generated responses for accuracy, relevance, consistency, reasoning quality, and adherence to task-specific instructions.
• Perform text and NLP annotation requiring close attention to semantics, context, tone, and intent.
• Cross-reference information and compare model outputs to identify factual, logical, and consistency issues.
• Apply detailed project guidelines and provide precise human feedback to support model improvement.

Freelance Engagement & Brand Growth Strategist - Self-Employed

• Advise organizations, entrepreneurs, and mission-driven brands on audience engagement and sustainable growth.
• Develop data-informed content strategies, brand messaging, and community engagement initiatives.
• Analyze engagement metrics to optimize content performance and audience retention.

Fundraising Division Manager - Amnesty International USA - Oakland, CA

• Led, mentored, and motivated a fundraising team supporting international human rights initiatives.
• Developed fundraising strategies spanning donor acquisition, retention, face-to-face fundraising, telefundraising, and digital outreach.
• Built donor relationships through empathy, mission-focused storytelling, and personalized engagement.
• Collaborated with communications teams on fundraising appeals aligned with human rights campaigns and emergency response efforts.
• Managed campaign budgets, analyzed donor data and KPIs, and identified opportunities using performance metrics.
• Recruited, trained, coached, and evaluated staff while maintaining ethical, financial, privacy, and compliance standards.

Assistant Caseworker - Immigration & Asylum Services - Ausländerbehörde - Bad Kreuznach, Germany

• Supported immigration and asylum case management for refugees and foreign national applicants.
• Collected and processed identity documents, travel records, and confidential physical and electronic case files.
• Scheduled interviews, medical examinations, legal appointments, and interpreter services.
• Explained administrative requirements to asylum seekers and coordinated with interpreters, social workers, healthcare providers, youth services, and law enforcement.
• Assisted with refugee housing placement while maintaining strict confidentiality and German data protection requirements.

Owner & Operations Manager - HomeSuite Cleaning Services

• Founded and managed a residential and commercial cleaning company, overseeing scheduling, marketing, budgeting, quality assurance, and client relationships.
• Managed day-to-day operations and service quality while building long-term customer relationships.

Linguistics Studies - Johannes Gutenberg University Mainz

General Studies Coursework - University of Maryland Global Campus (Rose Barracks)

Diploma - Bethel High School