Remote Online Bookkeeper Jobs in Springfield, MA

Job Title: Accountant (CPA/CA)

Job Type: Contract

Location: Remote

Job Summary: You'll use your tax expertise to help train next-generation AI systems. The core work is reading US sales and use tax statutes and defining exactly what an AI's formal translation of the law must capture to be correct. Work spans multiple state jurisdictions, with some federal provisions as well. No prior AI experience needed. Your ability to read a statute and break it into precise, testable requirements is what matters.

Key Responsibilities:

1. Read and interpret sales and use tax statutes and regulations across US state jurisdictions, and occasionally federal tax provisions, at the level of individual subsections.
2. Author rubrics: break a section of law into a checklist of discrete requirements the AI's translation must satisfy, grounded strictly in the statute text and written independently of the AI's output.
3. Assign severity to each requirement (critical vs. secondary vs. minor) based on genuine statutory weight, not defaulting everything to critical.
4. Review the AI's formal translation of a statute and score it pass/fail against your rubric, checking that conditions, thresholds, AND/OR logic, and exceptions are captured accurately.
5. Write clear, self-contained test scenarios (including edge cases) for failed criteria, with explicit facts, dates, amounts, and expected outcomes.
6. Identify and flag discrepancies, statutory exceptions, and genuine ambiguities in the law.
7. Work within a digital review platform, submitting structured written evaluations.

Required Skills and Qualifications:

1. Active CPA license, Chartered Accountant designation, or experience as a US tax attorney.
2. Sales and use tax or broader state and local tax statutory experience strongly preferred.
3. Proven ability to read and interpret tax statutes and regulations, not just prepare returns.
4. Comfort working with legal logic: conditions, thresholds, AND/OR structures, exceptions, and defined terms.
5. Strong written communication with a focus on precision. Another reviewer should reach the same conclusion from your criteria.
6. High attention to detail, especially around "except for" clauses and edge cases.
7. Comfort providing structured feedback through a digital review interface.

Preferred Qualifications:

1. Experience across multiple state tax jurisdictions.
2. Enrolled Agent designation, or federal tax experience relevant to the scenario-review track.
3. Direct experience reviewing or validating AI or technology-driven tax content.
4. Background in training teams or giving written feedback on legal/tax language.
5. Interest in the intersection of technology and tax compliance.