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Accounting Paid Consultant - Tax Controversy, Representation & Strategic Planning

Job in Chicago, Cook County, Illinois, 60601, USA
Listing for: LinkedIn
Part Time position
Listed on 2026-10-30
Job specializations:
  • Business
    AI Evaluation
Salary/Wage Range or Industry Benchmark: 110 USD Hourly USD 110.00 HOUR
Job Description & How to Apply Below

We are seeking experienced Tax Controversy Professionals and Tax Advisors (Tax Attorneys, CPAs, or Senior Tax Advisory Professionals) to provide expert insight as part of a project for our AI Marketplace. No preparation required - just your real-world experience.

This is a one-time, paid, project-based interview engaged on a contract basis - not a full-time role.

Location: U.S.

-based experts only

Engagement: One-time, project-based interview

Work Type: Remote

Estimated rate: $110/hr (prorated for the 45-minute task)

What You’ll Do

You’ll complete a ~45-minute recorded AI-led video interview where you explain how you actually do your work in practice.

This interview will focus on:

  • How you manage tax examinations, controversies, appeals, and taxpayer representation
  • How you research authority, evaluate evidence, and develop a response strategy
  • How you advise on entity structure, transactions, estates, and future tax planning
  • How you negotiate resolutions, document approvals, and hand off implementation

You will be asked to explain workflows specifically within: controversy intake, issue analysis, authority research, response strategy, taxpayer representation, negotiation, resolution, and forward-looking planning.

You should only apply if you can confidently walk through these areas step-by-step based on your own experience and respond to AI-led interview questions with depth, clarity, and real-world examples.

What We’re Looking For
  • 7+ years in tax controversy, representation, planning, and advisory services
  • Direct, hands-on experience in controversy intake, issue analysis, authority research, response strategy, taxpayer representation, negotiation, resolution, and forward-looking planning
  • Experience making or influencing decisions related to legal or technical position, documentation sufficiency, escalation, settlement or appeal strategy, entity structure, transaction planning, and client risk
  • Familiarity with tools such as: tax research platforms, tax preparation and workpaper systems, matter management, authority portals, document management, financial modeling, and secure client collaboration
  • Strong ability to clearly explain workflows, decisions, and reasoning
  • Experience owning or directly executing these workflows in a real production environment
  • Experience working in a relevant cross-functional environment
About the Interview

The interview is designed to elicit step-by-step explanations of real workflows and decision-making processes, with an emphasis on detailed, experience-based responses rather than high-level summaries.

This is a project-based engagement. Selected participants will be paid for completing a recorded AI-led video interview; hourly rates are estimates based upon anticipated time of completion. Participants will control their own schedule, provide their own tools to complete the interview, and may participate in other opportunities as they choose.

Once you complete the interview, we’ll send your video recording and transcript, along with AI-generated insights, to the internal research team and AI lab partner. This data will be used to generate a structured list of tasks associated with your profession and for AI model improvement.

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