# Tax Expert (CPA / EA)

> Weekday AI · Chicago, United States · Full-time · Posted 2026-09-26

**Salary:** INR 9,000,000–15,000,000

**Workplace:** on_site

**Department:** Weekday's Client via platform

## 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 experienced **Tax Subject Matter Expert** with 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 a **CPA 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 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.

What Makes You a Great Fit

-   **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.

## Apply

[Apply at Weekday AI](https://apply.workable.com/weekday-1/j/537EAC132B/apply)

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