Oliver T. Williams

Graphic Designer & Data Analyst

Data Analyst & Graphic Designer

317-914-8047 Chicago, IL (relocating Oct 2026) [email protected] olivertwilliams.com

Work Experience

Generalist Expert [Contract]

Aug 2026 – Present

Mercor

  • Conducted qualitative and visual evaluations of AI model outputs regarding UI/UX, visual hierarchy, and layout consistency.
  • Evaluated visual/multimodal model responses against established design standards and functional criteria.
  • Formulated detailed design tasks and provided structured feedback to refine model performance on design-centric requests.
  • Evaluated, annotated, and curated complex datasets to support AI model training and fine-tuning.
  • Maintained high data quality and throughput standards in structured evaluation and QA workflows.
  • Formulated edge-case tasks and benchmarked model outputs against strict accuracy guidelines.

AI Trainer [Contract]

Apr 2026 – Present

Handshake AI & DataAnnotation

  • Authored complex graphic design project briefs to stress-test AI model capabilities across 2D software including GIMP, Inkscape, and Krita.
  • Reviewed and graded AI-generated text and images for accuracy, quality, and logical flow while providing detailed written rationales for each decision.
  • Developed structured evaluation rubrics and scoring datasets to train machine learning models on professional design standards.

AI Trainer [Contract]

Apr 2026 – Present

DataAnnotation

  • Applying a dual background in data analytics and graphic design to evaluate and refine unreleased AI models through rigorous human-feedback data curation.
  • Evaluated the composition, lighting, and aesthetic quality of AI-generated imagery, specifically identifying structural inconsistencies, prompt adherence, and visual artifacts.
  • Critically reviewed and graded AI-generated text for factual accuracy, natural phrasing, and logical flow across a wide variety of complex topics.
  • Provided detailed, written rationales for model grading, contributing to high-quality datasets used to train and align language and vision models.

2D Design Specialist [Contract]

Apr 2026 – Jul 2026

Handshake AI

  • Authored complex graphic design project briefs to stress-test model capabilities and tool execution within 2D design software including GIMP, LibreSprite, Inkscape, and Krita.
  • Developed structured, binary evaluation rubrics and scoring datasets that directly train machine learning models to evaluate design outputs.
  • Translated advanced design workflows into deterministic, step-by-step verification processes used by automated systems to grade outputs and optimize model weights.

Tax Verification Associate

Feb 2026 – Apr 2026

Thomson Reuters

  • Reviewed and categorized sensitive tax data using Excel and internal software, consistently exceeding high-volume daily targets during peak tax season.

Graphic Design Intern

Dec 2024 – Feb 2025

City of Shorewood

  • Designed print and digital materials for city events including brochures, flyers, and social media graphics while ensuring adherence to municipal branding guidelines.
  • Standardized all public forms by converting them into accessible fillable PDFs using Adobe Acrobat Pro to improve office efficiency.

Drake Relays Logo Designer

Dec 2024 – May 2025

Drake University

  • Selected from 11 finalists to design the official logo and visual theme for the 2025 Drake Relays ("Racing Through Time").
  • Brand identity deployed across merchandise, campus signage, and digital platforms for an event drawing thousands of attendees.

Projects

Brushfactory

Aug 2026 – Present

Brushfactory.co

  • Designed and shipped a responsive web application (HTML/Tailwind/JS) to convert digital illustration brushes across major platforms, executing the complete UI/UX and brand identity from the ground up.
  • Built the backend conversion logic and test harness in Python to parse proprietary formats, measuring drift in brush size, spacing, and pressure response.

Freelance Branding & Design

Aug 2021 – Present

Various Clients

  • Designed tour and performance flyers for Minneapolis musicians Dessa and Jeremy Messersmith, delivered in print and digital formats.
  • Provided logo systems, brand guidelines, and promotional assets for clients including The Forged Group and Pyrkia Health.

Data Visualization & Modeling

Aug 2025 – Dec 2025

DMARC Food Pantry Network

  • Built a reproducible R pipeline to clean and analyze visitor logs from 90+ pantry locations, enriched with ACS Census demographic data.
  • Created Leaflet geospatial maps to identify service gaps and developed a Poisson regression model to forecast future pantry demand by region.