Founding Tax SME (Greater Chicago Area)

Chicago, IL | Full-Time | High-Growth Startup

· Base Salary: $100,000 - $200,000

· Equity: 0.50% - 2.00%

· Employment Type: Full-time

· Location: Chicago, IL (on site) - Relocation assistance may be available for the right candidate.

· Experience: 3+ years

· Work Authorization: U.S. Citizen or authorized to work in the U.S. without sponsorship now or in the future

· Health Benefits: Company covers 100% of employee medical, dental, and vision premiums

We're partnering with a venture-backed technology company that is rethinking how tax returns are prepared, reviewed, and filed. Backed by experienced founders and building in a highly specialized space, the team is creating modern infrastructure to replace legacy tax software used by accounting firms today.

This is not a traditional accounting role.

We're seeking a CPA who wants to move beyond return preparation and help shape the future of tax technology. You'll work directly with founders and engineers to solve complex tax challenges, influence product direction, and help build software that thousands of tax professionals may eventually rely on.

What You'll Do

• Serve as a key member of the founding team
• Partner closely with engineering to translate tax requirements into product functionality
• Identify edge cases, tax scenarios, and workflow improvements
• Prepare and review complex individual tax returns
• Test and validate tax calculations across a variety of scenarios
• Help shape product strategy and roadmap decisions
• Provide subject matter expertise on federal individual income tax and related entities

What We're Looking For

• CPA strongly preferred
• Experience preparing and reviewing individual tax returns
• Experience with professional tax software such as UltraTax, CCH Axcess, Drake, Lacerte, ProSeries, or similar platforms
• Strong understanding of complex 1040 tax situations
• Exposure to partnerships, K-1s, trusts, estates, or other complex tax structures is highly valued
• Comfortable working in a fast-paced, highly collaborative environment
• Passion for technology, automation, and improving how tax work gets done

Ideal Backgrounds

• Tax Manager
• Senior Tax Associate with review responsibilities
• Private Client Services / High-Net-Worth Tax professional
• Regional CPA firm professional
• Big 4 Private Client Services professional
• Tax professional with an interest in product, technology, or startups