Resume

BRIAN OLSON

Foundational LLM Evaluation Specialist | AI Quality Assurance Expert | Conversational UX Strategist

(406) 210-5480 | brian.olsonwriter@gmail.com | Kalispell, Montana, USA

LinkedIn: www.linkedin.com/in/brian-olson-b527408 | Portfolio: brianolsonwriter.com/

PROFESSIONAL SUMMARY: AI CONTENT STRATEGIST

FOUNDATIONAL LLM EVALUATION SPECIALIST and AI Content Strategist specializing in defining and enforcing “gold-standard” language for frontier AI models (GPT, Claude, Gemini). With over 2 years of strategic LLM Quality Assurance experience, I focus on model guardrails, adversarial testing, and conversation design. Recognized as a “creative jolt” and “unflappable” self-starter who excels at translating complex, technical material into engaging, clear communication. Seeking a high-impact, remote role in AI Content Strategy, LLM Quality Assurance, or Conversational UX Design.

CORE EXPERTISE

LLM & AI STRATEGY Conversational UX & Content Technical & Tools Linguistic & Critical Reasoning
LLM Evaluation & Editing (1,000+ Hrs) Conversational Copy & Bot UX Prompt Design & Refinement Content Strategy & Tone Frameworks
Adversarial Testing & Model Guardrails Multi-Turn Dialogue Design Kontent, SurferSEO, Clearscope Analytical Judgment & Fact-Checking
RAG Quality Assurance Voice, Tone, and Microcopy Refinement Grammarly, ChatGPT, Gemini, Copilot Non-Idiomatic Spanish Fluency
AI Quality Assurance Specialist Intent Mapping and Fallback Strategies Dialogflow, Voiceflow (Dabbling/Training) Deep Editorial & Style Guide Adherence

PROFESSIONAL EXPERIENCE

AI Content & Chatbot Evaluation Specialist (Freelance · Contract)

July 2023 – Present (2 years 4 months)

  • Foundational Model Evaluation & Rubric Design: Developed evaluation rubrics and grading scaffolding for large-scale projects. Used RAG (Retrieval-Augmented Generation) sources to inform precise prompts, guiding evaluators to grade and improve model responses for core LLMs (GPT, Claude, Gemini).
  • Enterprise AI Safety & Bias Detection: Conducted adversarial testing and prompt jailbreaking to strengthen model guardrails, directly mitigating risks of misinformation and harmful biases.
  • Conversational UX & Search Optimization: Tested and optimized multi-turn dialogue flows, and refined AI retrieval models by rating responses for relevance and search intent alignment.
  • Quality Assurance: Provided structured feedback and ensured factual accuracy and contextual coherence across all AI outputs, resulting in high-quality data contribution.

Writer, Stay Alfred

November 2017 – January 2020 (2 years 3 months) | Spokane, WA Area

  • Hired for expertise in crafting “long format blog writing to 140-character punchy tidbits” (VP of Marketing).
  • Took “ownership of gathering information” and writing comprehensive in-unit handbooks, requiring enormous initiative and social skill (Manager).
  • Wrote all on-brand copy for email campaigns, native app content, signage, and UX procedural content, maintaining a cohesive voice during high growth.

Product Writer & Content Strategist (Freelance & In-House: Amazon, Citrix, CenturyLink)

August 2002 – Present

  • Technical Content Management: Managed all technical writing for a series of complex cloud networking white papers for Citrix. Praised for “understanding of communication and language” despite heady material (Teammate).
  • AI-Adjacent Content (2020-2023): Executed HITL content writing projects for clients like Roami and Palindrome, utilizing tools like ChatGPT, Grammarly, and Clearscope to optimize and refine output.
  • Amazon Product Writing (7 years): Wrote high-converting web product-page copy, guides, and creative advertising; performed in-depth product research, and ensured content complied with rigorous style guides and SEO standards.

EDUCATION & PROFESSIONAL DEVELOPMENT

Gonzaga University

BA, Spanish Literature (1989 – 1993)

Graduate Studies: Teaching Languages and Linguistics (1995 – 1996)
Completed 21 credits toward a teaching certificate; focused on language pedagogy and instructional theory.

Additional Education & Creative Focus

Flathead Valley Community College: 16 Credits (4 Courses) in Creative Writing (Poetry and Fiction) – 2003–2011.

Certifications & Specialized Training

  • Conversation & UX Design:
    • Intro To Conversation Design (Conversational Design Institute)
    • Getting Started in User Experience / Finding a Job in User Experience
  • Generative AI & Prompt Engineering:
    • Prompt Engineering: How to Talk to the AIs
    • Introduction to Prompt Engineering for Generative AI
  • Advanced Content Strategy:
    • Writing White Papers / Writing Case Studies
    • SEO: Keyword Strategy / Danny Sullivan on SEO

Instructional & Cross-Cultural Experience (1994-1998)

  • Pedagogy & Instructional Structure: Applied structural language principles while teaching ESL at Spokane Community College (night classes) and Language Arts/GED Prep as a Paraprofessional at Spokane Juvenile Detention Center.
  • Cultural Fluency: Taught English to Japanese students (2 years) and English Language & Literacy to forty Russian/Vietnamese political refugees, demonstrating strong cross-cultural communication skills.
  • Functional Spanish: Functional fluency for non-idiomatic contexts.

Field Certifications (Domain Expertise)

  • Fully Certified PSIA Ski Instructor
  • American Avalanche Association – Level 1 Certified
  • Whitewater Raft Guide & Swift Water Rescue Training