About this opportunity
Confidential lists this U.S.-Based Accountant (CPA/CA) opportunity in Fort Sheridan, Illinois. Review the employer’s description below for duties, qualifications and application requirements.
Job description
Role Overview Apply U.S. tax-law expertise to help evaluate and improve AI-powered tax solutions. You will translate sales and use tax statutes into precise, testable requirements, then assess whether an AI system’s formal interpretation accurately reflects the law across multiple state jurisdictions and, at times, federal provisions. Prior AI experience is not required.
Key Responsibilities Interpret U.S. sales and use tax statutes and regulations, including individual subsections, across state jurisdictions and occasional federal tax provisions.
Create statute-grounded scoring rubrics that break legal text into discrete requirements an AI translation must meet, independently of the AI output.
Classify rubric requirements as critical, secondary, or minor according to their actual statutory importance.
Review formal AI translations of statutes and assign pass or fail outcomes against the rubric.
Verify accurate treatment of conditions, thresholds, AND/OR logic, exceptions, and defined terms.
Write self-contained test scenarios for failed criteria, including edge cases, explicit facts, dates, amounts, and expected results.
Identify and document discrepancies, statutory exceptions, and genuine legal ambiguities.
Submit structured written evaluations through a digital review platform.
Qualifications Active CPA license, Chartered Accountant designation, or experience as a U.S. tax attorney.
Demonstrated ability to interpret tax statutes and regulations, beyond preparing tax returns.
Strong written communication and analytical reasoning, with criteria precise enough that another reviewer can reach the same conclusion.
Exceptional attention to detail, particularly for exception clauses and edge cases.
Comfort applying legal logic involving conditions, thresholds, AND/OR structures, exceptions, and defined terms.
Comfort delivering structured feedback through a digital review interface.
Sales and use tax experience, or broader state and local tax statutory experience, is strongly preferred.
Preferred: experience across multiple state tax jurisdictions, Enrolled Agent designation or relevant federal tax experience, validation of AI or technology-driven tax content, training teams or providing written feedback on legal or tax language, and interest in technology and tax compliance.
Work Terms Remote contract engagement.
Work focuses on U.S. sales and use tax law and related federal provisions.
Compensation $65 to $70 per hour.
Application Process Apply using an email address or an available third-party sign-in option. Continuing an application confirms agreement to the candidate Terms and Privacy Policy.
Who can apply
Review the original listing for work authorization, qualifications and employer requirements.