Tax Strategy and Compliance
Chicago, Cook County, Illinois, 60601, USA
Listed on 2026-11-06
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Finance & Banking
Tax Accountant, Tax Manager, Tax Advisor, Accounting & Finance -
Accounting
Tax Accountant, Tax Manager, Tax Advisor, Accounting & Finance
Position: E2C-EA37:
Enrolled Agent/Tax Strategy and Compliance
Location: Remote
Job Type: Full
-Time, Independent Contractor
Work Schedule: 40hrs/week, Within PST or CST
Who we areE2C International is a US-based company committed to providing a variety of cost-efficient, professionally trained, motivated remote workers for individuals and their organizations so they can focus on growing their businesses. We pride ourselves in assisting companies in reducing costs and increasing efficiency, leading to massive growth. Our strength comes from our global community and our power is driven by leveraging that to connect our clients with top talent worldwide.
JobPurpose and Role
We are seeking an experienced Enrolled Agent / Tax Strategy responsible for handling complex individual and entity tax matters for high-net-worth founders and family clients. The role focuses on tax return preparation, multi-state compliance, tax planning and projections, IRS/state representation, and improving the firm’s processes and review standards.
The ideal candidate has strong experience with complex individual and business returns, trusts, IRS matters, process improvement, and AI-assisted tax workflows.
Key Responsibilities- Prepare and review individual, S corporation, partnership, trust, and multi-state returns for founder and family clients.
- Build projections and planning models: entity selection, reasonable compensation, retirement plan stacking, Roth conversion timing, charitable structures, and pre-exit planning including Section 1202 and equity compensation.
- Represent clients before the IRS and state agencies.
- Design and document the firm's workpaper standards, review checklists, and intake process.
- Work inside AI-assisted workflows, reviewing machine-prepared work critically and improving the system rather than working around it.
- Explain complex positions to sophisticated clients in plain English.
- 5+ years of experience in tax, with the last several spent on complex individual and entity work. Depth beats years: a six-year EA who has only ever worked complex files is a better fit than a twenty-year EA from a volume shop.
- Has personally handled IRS notices, examinations, or collection matters.
- Comfortable with trusts and fiduciary returns; does not need to be an estate specialist.
- Has built or improved a firm's process, templates, or review system at least once.
- Comfortable with technology and automation; curious rather than defensive about AI tools.
- Has personally handled IRS notices, examinations, or collection matters
- Comfortable with trusts and fiduciary returns
- Has built or improved a firm's process, templates, or review system
- Curious about technology, automation, and AI tools, and able to say when you trust their output and when you don't
- Experience with Pro Connect Tax, Canopy, Filed, Claude, or Google Workspace (none are required)
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