Tax Tech Expert (CPA/EA) - U.S. Returns & Product Insight

Weekday AI; Chicago (IL); On-site; USD 120,000 - 180,000; Full time

Job summary

Weekday AI is seeking an experienced Tax Subject Matter Expert to help shape a modern tax technology platform. You will bring deep expertise in U.S.

individual income tax preparation and tax return review, collaborating with engineering and product teams to translate complex rules and real‑world workflows into accurate, intuitive product experiences. This role is ideal for a CPA or seasoned Enrolled Agent who has worked through multiple tax seasons, understands practical tax preparation, and can

Qualifications

• 6+ years of hands-on experience preparing and reviewing U.S. individual income tax returns across multiple full tax seasons.
• CPA with a tax-focused career; experienced Enrolled Agents (EA) with strong individual tax expertise may also be considered.
• Strong understanding of U.S. federal individual income tax laws, rules, forms, and tax preparation workflows.
• Extensive experience using professional tax software such as Drake, UltraTax, CCH, Lacerte, ProSeries, or similar platforms.
• Proven experience reviewing tax returns, not only preparing them.
• Strong ability to identify tax discrepancies, unusual scenarios, edge cases, and potential calculation issues.

Responsibilities

• Prepare and review U.S. individual income tax returns across a range of scenarios.
• Identify complex tax situations and gaps in product logic.
• Validate tax engine calculations against professional software.
• Compare results with platforms like Drake, UltraTax, CCH, Lacerte, ProSeries.
• Investigate discrepancies and communicate expected tax treatment to engineering teams.
• Translate practical tax workflows into actionable product feedback.
• Explain U.S. federal tax rules to engineers and product teams.
• Contribute to tax workflow improvements and user experience enhancements.
• Test new features and tax logic from a tax-practitioner perspective.
• Develop comprehensive test scenarios covering common and complex tax situations.

Skills

U.S. tax expertise

CPA/EA credentials

Tax return review

Technical communication

Analytical thinking

Proficiency with tax software

UX feedback for tax tech

Tax software testing

Education

CPA certification

Enrolled Agent (EA)

Tools

Drake

UltraTax

CCH

Lacerte

ProSeries

Job description

Weekday AI is seeking an experienced Tax Subject Matter Expert to help shape a modern tax technology platform. You will bring deep expertise in U.S.

individual income tax preparation and tax return review, collaborating with engineering and product teams to translate complex rules and real‑world workflows into accurate, intuitive product experiences. This role is ideal for a CPA or seasoned Enrolled Agent who has worked through multiple tax seasons, understands practical tax preparation, and can