Founding Tax SME

Stealth AI Startup; Chicago (IL); On-site; USD 90,000 - 130,000; Full time

Benefits offered by this job

Relocation assistance

Full health benefits

Job summary

Stealth AI Startup in Chicago is building cutting-edge tax technology and seeks a CPA to move beyond traditional return work into product-focused solutions. You will work closely with founders and engineers to translate tax requirements into software features, review complex 1040s, and help shape the roadmap in a fast-paced, collaborative environment.

Relocation assistance may be available for the right candidate, and the role is on-site in Chicago.

Qualifications

• CPA strongly preferred and active license.
• Experience preparing and reviewing individual tax returns.
• Familiarity with professional tax software (UltraTax, CCH Axcess, Drake, Lacerte, ProSeries).
• Strong understanding of complex 1040 scenarios and related entities.

Responsibilities

• Serve as a key member of the founding team.
• Partner with engineering to translate tax requirements into product features.
• Identify edge cases, tax scenarios, and workflow improvements.
• Prepare and review complex individual tax returns.
• Test and validate tax calculations across scenarios.
• Help shape product strategy and roadmap decisions.

Skills

CPA certification

Tax return preparation

Tax planning & review

Tax software experience

Product collaboration

Education

CPA license

Tools

UltraTax

CCH Axcess

Drake

Lacerte

ProSeries

Job description

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

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
• Tax professional with an interest in product, technology, or startups