Tax Expert (CPA / EA)

Weekday AI; United States; On-site; USD 9,000,000 - 15,000,000; Full time

Benefits offered by this job

Equity in startup

Direct collaboration with founders and

Influence on product roadmap

Job summary

Weekday AI is seeking experienced tax experts to join our client-focused team in a startup setting, shaping the future of tax accounting within a product-centric platform.

You will review returns, identify edge cases, and work closely with engineers to map real-world tax workflows into product improvements, bringing your CPA/EA credentials and deep U.S. tax knowledge to the table.

Qualifications

• 6+ years of experience preparing individual tax returns using professional tax software.
• Experience reviewing tax returns, not just preparing them.
• Strong understanding of U.S. federal individual income tax.

Responsibilities

• Prepare and review individual income tax returns.
• Identify tax edge cases, complex scenarios, and product improvement opportunities.
• Validate engine output against legacy tax software and flag discrepancies.
• Translate hands-on tax workflow into UX feedback for the product roadmap.
• Collaborate with engineers to explain tax rules and outcomes.

Skills

Individual Income Tax Preparation

Tax Return Review

U.S. Federal Tax Law

Edge Case Identification

Product & UX Feedback

Education

CPA (Certified Public Accountant)

EA (Enrolled Agent)

Tools

Drake Tax Software

UltraTax

CCH ProSystem fx

Lacerte

ProSeries

Job description

𝗧𝗵𝗶𝘀 𝗿𝗼𝗹𝗲 𝗶𝘀 𝗳𝗼𝗿 𝗼𝗻𝗲 𝗼𝗳 𝘁𝗵𝗲 𝗪𝗲𝗲𝗸𝗱𝗮𝘆'𝘀 𝗰𝗹𝗶𝗲𝗻𝘁𝘀

Salary range: Rs 9000000 - Rs 15000000 (ie INR 900-1500 LPA)

Experience: 6+ yrs

Location: United States

Job Type: Full-time

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 & Perks

• 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.

Required Skills

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

Must-have skills

CPA, tax return preparation, Tax Softwares

Good-to-have skills

U.S. Federal Tax Law, Edge Case Identification, Drake Tax Software