Tax Expert (CPA / EA)

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.

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.