AI UX Researcher (

Bold Insight Inc.; Downers Grove (IL); Remote; USD 165,000 - 248,000; Full time

Job summary

Bold Insight Inc. seeks a contract AI UX researcher to evaluate enterprise AI platforms and produce client-ready deliverables. You will work with the project lead to expand research capacity, build synthetic test data, and translate model behavior into actionable guidance.

You will design test fixtures, assess agent performance, and co-present findings to stakeholders, ensuring evidence-based recommendations for clients.

Qualifications

• 6+ years in UX research or related field with recent AI research focus.
• Experience turning technical observations into clear recommendations.
• Location in Chicagoland preferred but remote contractors considered.
• Authorized to work in the United States without sponsorship.

Responsibilities

• Execute heuristic evaluations on enterprise AI platforms.
• Architect test fixtures and grade agent performance.
• Assemble deliverables and manage background tools and repositories.
• Develop and present user journeys and usability scorecards.
• Co-present findings to non-technical stakeholders.

Skills

AI tinkering

Analytical rigor

Systems-level adaptability

Token & context economics

Synthetic data engineering

Artifact assembly

Tools

Claude Cowork

Slack AI

Microsoft Copilot

Claude Code

MCP connectors

VM sandboxing

API permissions

Job description

Evaluate enterprise AI platforms and give clients clear evidence their AI works for the people using it.

We are looking for a contract AI UX researcher to work directly with our project lead. You will help us expand our research capacity by evaluating AI systems, building synthetic test data, and producing client-ready deliverables.

Why this role matters

AI is changing how people experience products, and our clients need clear evidence that their AI works for the people using it. You will work alongside our team to assess how enterprise AI products behave in practice. Your work will range from heuristic evaluations to collecting test data and managing the context that AI tools rely on. The result: clients understand what their AI can and cannot do.

What you’ll do

• Execute heuristic evaluations on enterprise AI platforms including Claude Cowork, Slack AI, and Microsoft Copilot.
• Architect test fixtures and grade agent performance on capability, fidelity, and identity.
• Manage repositories and orchestrate background tools to assemble deliverables.
• Experience map critical user journeys (CUJs) and translate model behavior into executive-ready usability scorecards.
• Co-present technical findings to non-technical stakeholders on the fly.

What you’ll bring

• AI tinkering : Demonstrate active experimentation with LLMs, CLI tools (like Claude Code), and agent orchestration.
• Analytical rigor : Contextualize AI outputs against answer keys, spot hallucinations, and grasp the limits of probabilistic models.
• Systems-level adaptability: Debug work environments spanning MCP connectors, VM sandboxing, and API permissions.
• Token & context economics : Structure prompts, local repositories, and agent memory to manage context windows efficiently.
• Synthetic data engineering : Skill in using LLMs to script realistic testing environments, such as generating JSON chat histories with seeded, checkable facts.
• Artifact assembly : The ability to orchestrate agents to output structured HTML presentation canvases, native Office files, and polished research reports.

Requirements

• Experience: 6+ years in UX research or related field, with a demonstrated recent focus on AI research. Background in UX and AI system evaluation, and a record of turning technical observations into clear recommendations.
• Location: Chicagoland-based preferred, but open to remote contractors for the right candidate.
• Work authorization: Authorized to work in the United States now and in the future, without visa sponsorship.

This is a contract position. Chicagoland-based preferred, but open to U.S.-based remote candidates for the right fit.

We work in virtually every industry across hundreds of products.

Collaborative team

Incredibly collaborative and supportive team and fun and casual work environment.