Tax Expert (CPA / EA)

Weekday 1; Chicago (IL); On-site; USD 108,000 - 180,000; Full time

Job summary

Weekday 1 is seeking a Tax Subject Matter Expert with deep expertise in U.S. individual income tax preparation to help shape a modern tax technology platform.

The role suits a CPA or experienced Enrolled Agent who has worked through multiple tax seasons and understands practical filing and review workflows. You will translate tax rules into product and UX feedback, validate engine outputs, and collaborate with engineering and product teams to improve accuracy and usability.

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.
• Excellent understanding of how tax rules translate into practical preparation workflows and software functionality.
• Strong analytical and problem-solving skills with exceptional attention to accuracy and detail.
• Ability to clearly explain complex tax concepts and expected outcomes to engineers and product teams.
• Strong product mindset with the ability to translate tax-practitioner experience into practical UX and product recommendations.
• Comfortable working closely with technology, product, and engineering teams in a collaborative environment.
• Ability to work effectively in a small, fast-moving, early-stage environment with a high degree of ownership.
• Strong interest in the intersection of tax, technology, product development, and automation.
• Excellent communication skills and the ability to challenge product assumptions constructively based on professional tax expertise.

Responsibilities

• Prepare and review U.S. individual income tax returns across a range of tax scenarios.
• Identify complex tax situations, edge cases, exceptions, and scenarios that could expose gaps in product logic.
• Validate tax engine calculations and outputs against professional tax software and established tax practices.
• Compare results with platforms such as Drake, UltraTax, CCH, Lacerte, ProSeries, or similar professional tax applications.
• Investigate discrepancies and communicate expected tax treatment and outcomes to engineering teams.
• Translate practical tax preparation workflows and professional experience into actionable product and UX feedback.
• Work closely with engineers to explain U.S. federal individual tax rules, calculations, dependencies, and exceptions.
• Participate in product discussions and help identify improvements to tax workflows, functionality, and user experience.
• Review product behaviour against real-world tax preparation scenarios and identify potential accuracy or usability issues.
• Help test new features, tax logic, workflows, and product releases from a tax-practitioner perspective.
• Contribute to building comprehensive test scenarios covering common, complex, and unusual tax situations.
• Provide subject-matter expertise during product development and help ensure tax functionality reflects professional preparation practices.

Skills

U.S. tax law expertise

Tax return review

Communication with engineers

Problem-solving

Education

CPA certification

EA eligibility

Tools

Drake

UltraTax

CCH

Lacerte

ProSeries

Job description

𝗧𝗵𝗶𝘀 𝗿𝗼𝗹𝗲 𝗶𝘀 𝗳𝗼𝗿 𝗼𝗻𝗲 𝗼𝗳 𝘁𝗵𝗲 𝗪𝗲𝗲𝗸𝗱𝗮𝘆'𝘀 𝗰𝗹𝗶𝗲𝗻𝘁𝘀

𝗦𝗮𝗹𝗮𝗿𝘆 𝗿𝗮𝗻𝗴𝗲: 𝗥𝘀 𝟵𝟬𝟬𝟬𝟬𝟬𝟬 - 𝗥𝘀 𝟭𝟱𝟬𝟬𝟬𝟬𝟬𝟬 (𝗶𝗲 𝗜𝗡𝗥 𝟵𝟬-𝟭𝟱𝟬 𝗟𝗣𝗔)

Experience: 6+ yrs

Location: Chicago, Illinois, United States

Job Type: Full-time

We are looking for an experiencedTax Subject Matter Expertwith deep expertise in U.S. individual income tax preparation and tax return review to help shape the development of a modern tax technology platform.

This role is ideal for aCPA or experienced Enrolled Agent (EA)who has worked through multiple tax seasons and understands the practical realities of preparing and reviewing individual tax returns. You will bring hands-on tax expertise into a technology and product environment, working closely with engineering and product teams to translate tax rules, complex scenarios, and real-world workflows into accurate and intuitive product experiences.

Requirements

Key Responsibilities

• Prepare and reviewU.S. individual income tax returnsacross a range of tax scenarios.
• Identify complex tax situations, edge cases, exceptions, and scenarios that could expose gaps in product logic.
• Validate tax engine calculations and outputs against professional tax software and established tax practices.
• Compare results with platforms such asDrake, UltraTax, CCH, Lacerte, ProSeries, or similar professional tax applications.
• Investigate discrepancies and communicate expected tax treatment and outcomes to engineering teams.
• Translate practical tax preparation workflows and professional experience into actionable product and UX feedback.
• Work closely with engineers to explainU.S. federal individual tax rules, calculations, dependencies, and exceptions.
• Participate in product discussions and help identify improvements to tax workflows, functionality, and user experience.
• Review product behaviour against real-world tax preparation scenarios and identify potential accuracy or usability issues.
• Help test new features, tax logic, workflows, and product releases from a tax-practitioner perspective.
• Contribute to building comprehensive test scenarios covering common, complex, and unusual tax situations.
• Provide subject-matter expertise during product development and help ensure tax functionality reflects professional preparation practices.

What Makes You a Great Fit

• 6+ years of hands-on experiencepreparing 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 ofU.S. federal individual income tax laws, rules, forms, and tax preparation workflows.
• Extensive experience using professional tax software such asDrake, 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.
• Excellent understanding of how tax rules translate into practical preparation workflows and software functionality.
• Strong analytical and problem-solving skills with exceptional attention to accuracy and detail.
• Ability to clearly explain complex tax concepts and expected outcomes toengineers and product teams.
• Strong product mindset with the ability to translate tax-practitioner experience into practicalUX and product recommendations.
• Comfortable working closely with technology, product, and engineering teams in a collaborative environment.
• Ability to work effectively in asmall, fast-moving, early-stage environmentwith a high degree of ownership.
• Strong interest in the intersection oftax, technology, product development, and automation.
• Excellent communication skills and the ability to challenge product assumptions constructively based on professional tax expertise.