[Hiring] Tax Expert @Weekday AI

Role Description

Seeking tax experts who have lived through tax seasons firsthand and want to help shape the future of tax accounting. You'll work closely with the founding team to review returns, identify edge cases, and translate real-world tax workflows into product improvements. This is not a traditional accounting firm role; you'll bring your tax expertise into the product-building process, working at the intersection of tax, technology, and product, effectively serving as a subject matter expert embedded on the engineering team.

Key Responsibilities

• Prepare and review individual income tax returns.
• Identify tax edge cases, complex scenarios, and ways to break the product.
• Validate engine output against legacy professional tax software (UltraTax, CCH, Drake, Lacerte, ProSeries, or similar) and flag discrepancies.
• Bring your tax preparation experience to help shape the product roadmap and UX.
• Work directly with engineers to explain tax rules and expected outcomes.

Qualifications

• Certified Public Accountant (CPA) with a tax-focused career (not audit, payroll, or bookkeeping). Experienced Enrolled Agents (EA) may also be considered.
• 6+ years of experience preparing individual tax returns using professional tax software such as Drake, UltraTax, CCH, Lacerte, ProSeries, or similar platforms, across multiple full tax seasons (January–April 15).
• Experienced reviewing tax returns, not just preparing them.
• Strong understanding of U.S. federal individual income tax.
• An eye for product and user experience, with the judgment to translate hands-on tax workflow experience into concrete UX feedback.
• Comfortable working in a small, early-stage startup environment.

Benefits

• Meaningful ownership over how a modern tax platform gets built, not just how one return gets filed.
• Equity, on a sliding scale for candidates flexible on base compensation.
• Direct, ongoing collaboration with the founders and engineering team.
• A seat at the table shaping the product ahead of the upcoming tax season.

Requirements

• Individual Income Tax Preparation
• Tax Return Review
• U.S. Federal Tax Law
• Drake Tax Software
• UltraTax
• CCH ProSystem fx
• Lacerte
• ProSeries
• Edge Case Identification
• Product & UX Feedback
• CPA
• Enrolled Agent (EA)
• Startup Environment