AI Trainer – Tax Advisors / Preparers

Senior AI Trainer – Tax Advisors / Preparers

Industry: Artificial Intelligence (AI) / Tax & Professional Services

Role Type: Short-Term Contract

Engagement Type: Independent Contractor

Location: Remote – United States (Approved States Only)

Engagement Duration: Up to 9 Weeks

Compensation: USD 82/hour

Working Hours: Minimum 4 hours/day, up to 40 hours/week

Client Summary
Our client, Turing, is one of the world's fastest-growing AI companies, focused on accelerating the advancement and deployment of powerful AI systems.
The company works with leading AI laboratories to advance frontier AI capabilities across areas such as reasoning, coding, agentic behavior, multimodality, multilinguality, STEM, and frontier knowledge. It also applies this work to develop real-world AI systems designed to solve mission-critical business challenges.

Role Overview
We are seeking experienced Tax Advisors and Tax Preparers to join a specialized AI training and evaluation project.
As a Senior AI Trainer, you will apply your expertise in US taxation to create, evaluate, calibrate, and refine complex tax-related tasks used to train advanced AI systems. You will develop high-difficulty tax scenarios and gold-standard solutions while ensuring AI-generated outputs are technically accurate, compliant with applicable US tax regulations, and reflective of real-world professional tax workflows.
The successful candidate will combine deep US tax expertise with strong analytical judgment and written communication skills. You will also review the work of other contributors, maintain quality standards, and identify complex or ambiguous tax issues requiring escalation to the Functional SME Lead.

Key Responsibilities

AI Training & Expert Task Development

• Develop high-difficulty, realistic tax tasks and scenarios for AI training and evaluation.
• Create gold-standard solutions based on applicable US tax laws, regulations, professional standards, and practical tax workflows.
• Develop complex scenarios covering tax planning, compliance, tax research, tax positions, and regulatory interpretation.
• Design tasks that test AI systems' ability to analyze complex tax situations and provide accurate, context-aware conclusions.
• Ensure all tasks reflect realistic challenges encountered by professional tax advisors and preparers.

Tax Analysis & Technical Review

• Analyze complex US tax scenarios involving individuals, partnerships, corporations, and multistate taxation.
• Review AI-generated tax responses for technical accuracy, completeness, consistency, and regulatory alignment.
• Evaluate tax positions and conclusions against applicable US tax rules and professional tax practices.
• Identify incorrect interpretations, unsupported assumptions, missing considerations, and technical inconsistencies.
• Apply professional judgment to determine whether proposed tax treatments are reasonable and defensible.

Tax Planning & Compliance Evaluation

• Develop and evaluate scenarios involving federal and state tax compliance and tax planning.
• Assess AI recommendations relating to tax-efficient structures, deductions, credits, income recognition, and other relevant tax considerations.
• Review proposed tax strategies for technical accuracy, practicality, and compliance risks.
• Evaluate whether AI-generated recommendations appropriately consider the taxpayer's circumstances and objectives.
• Identify potential tax planning opportunities, limitations, and areas requiring additional professional review.

Individual, Business & Multistate Taxation

• Apply expertise across individual income taxation, partnership taxation, corporate taxation, and multistate tax matters.
• Evaluate complex taxpayer scenarios involving multiple entities, jurisdictions, income sources, and tax considerations.
• Review AI outputs for appropriate treatment of different taxpayer structures and circumstances.
• Assess whether multistate tax recommendations appropriately address relevant state tax considerations and potential compliance obligations.
• Create challenging scenarios that test AI reasoning across different taxpayer profiles and tax structures.

Tax Research & Regulatory Interpretation

• Develop tasks requiring interpretation and application of complex US tax regulations.
• Evaluate AI-generated tax research and conclusions for accuracy and appropriate interpretation of applicable authorities.
• Assess whether tax conclusions are supported by relevant rules, regulations, and professional tax principles.
• Identify situations where additional research or professional judgment is required.
• Review outputs for appropriate handling of ambiguity, exceptions, limitations, and changing regulatory requirements.

Tax Return & Tax Position Review

• Review complex tax return scenarios and identify potential technical or compliance issues.
• Evaluate proposed tax positions for accuracy, consistency, and potential risk.
• Identify missing information, inconsistencies, calculation issues, and questionable tax treatments.
• Assess whether proposed positions are appropriately supported by the available facts and applicable tax rules.
• Provide expert corrections and explanations where AI-generated outputs do not meet professional standards.

AI Output Evaluation & Quality Assurance

• Evaluate AI-generated responses using established quality standards, rubrics, and evaluation frameworks.
• Assess outputs for technical accuracy, reasoning quality, completeness, clarity, and practical applicability.
• Identify errors, gaps, inconsistencies, and unsupported conclusions.
• Provide clear expert feedback explaining why an output is correct, incorrect, incomplete, or requires modification.
• Ensure completed tasks and evaluations consistently meet the project's required quality bar.

Team Calibration & Quality Oversight

• Review and calibrate the work of other team members to maintain consistent quality standards.
• Provide constructive feedback on task design, tax analysis, solutions, and evaluation decisions.
• Support day-to-day quality assurance within the functional pod.
• Identify recurring quality issues and recommend improvements to task development and evaluation processes.
• Maintain consistency in the application of project rubrics and tax-related evaluation standards.

Escalation & Expert Judgment

• Identify genuine edge cases, complex tax issues, and situations where established evaluation criteria may be unclear.
• Escalate rubric ambiguities and technically complex cases to the Functional SME (Expert) Lead.
• Provide clear context and supporting analysis when escalating an issue.
• Exercise independent professional judgment while recognizing situations that require additional expert review.
• Incorporate SME guidance and calibration feedback into subsequent tasks and evaluations.

Professional Tax Communication

• Explain tax conclusions in clear, accurate, and practical language.
• Translate complex tax concepts into structured explanations that can be understood by different audiences.
• Develop realistic professional tax communications and written responses.
• Ensure explanations distinguish between established tax rules, assumptions, and areas requiring further professional judgment.
• Maintain a high standard of clarity, precision, and professionalism in all written deliverables.

Required Qualifications & Experience

• Professional Tax Experience
• 8–15 years of US tax experience in public accounting, corporate tax, or an in-house tax function.
• Extensive experience with complex US taxation matters.

Strong practical knowledge across:

• Individual taxation, Partnership taxation, Corporate taxation, Multistate taxation
• Demonstrated experience with tax planning, compliance, research, and regulatory interpretation.
• Proven ability to review complex tax returns and evaluate technical tax positions.

• Active CPA (Certified Public Accountant) or Enrolled Agent (EA) credential is required.
• JD or LLM in Taxation is an advantage.
• Candidates must maintain the required professional credentials applicable to their practice.

• Strong understanding of US federal taxation.
• Strong knowledge of relevant state and multistate tax considerations.
• Demonstrated ability to interpret complex US tax regulations.
• Strong understanding of tax compliance requirements and tax planning principles.
• Ability to identify technical, regulatory, and compliance risks.
• Ability to evaluate complex tax positions and determine appropriate treatment based on the available facts.

• Exceptional analytical and problem-solving abilities.
• Strong professional judgment when evaluating complex tax situations.
• Ability to identify subtle technical issues and potential compliance risks.
• Strong attention to detail when reviewing tax-related information and outputs.
• Ability to distinguish between technically correct, incomplete, and potentially misleading tax conclusions.

• Excellent written communication skills.
• Ability to explain complex tax conclusions clearly, accurately, and practically.
• Strong ability to document reasoning and provide structured feedback.
• Ability to create realistic tax scenarios and professional-quality reference solutions.

• Experience in AI evaluation, data annotation, content review, quality assurance, or a related analytical role is preferred but not required.
• Previous AI training experience is not mandatory; strong professional tax expertise is the primary requirement.

• Bachelor's degree or equivalent practical experience in any field.
• Additional professional qualifications in accounting, taxation, law, or a related discipline are advantageous.

• US Taxation
• Tax Planning & Compliance
• Tax Research
• Individual Taxation
• Partnership Taxation
• Corporate Taxation
• Multistate Taxation
• Tax Return Review
• Tax Position Analysis
• Regulatory Interpretation
• Risk Assessment
• Analytical Reasoning
• Quality Assurance
• Professional Judgment
• Written Communication
• AI Evaluation