Remote Tax Manager

About Outlook Accounting & Taxes Corporation

Outlook Accounting & Taxes Corporation is a leading accounting and consulting firm based in the Chicagoland area, built on the core values of responsibility, professionalism, and client satisfaction. Our mission is to help individuals and businesses achieve financial freedom, optimize tax outcomes, and make informed financial decisions. From personal income tax preparation to complex business services, Outlook provides expert guidance tailored to each client’s unique needs.

Outlook Accounting & Taxes Corporation is seeking an experienced, driven, and independent Tax Manager to join our fully remote team. This leadership role is ideal for professionals who thrive in a dynamic and lean environment, enjoy working with a diverse range of clients, and are passionate about mentoring teams and improving processes. As a Tax Manager, you will work across a variety of client engagements and specialize in taxation and financial insights, providing both tax consulting and tax compliance services.

You will oversee client relationships, guide tax strategy, and contribute to the continued growth and operational excellence of the firm. This role offers a growth pathway to Senior Manager / Director based on performance.

• Prepare and/or review complex tax filings, including Individual (1040), Corporate (1120), S Corporation (1120S), Partnership (1065), Non‑Profit (990), and Trust/Estate (1041) returns.
• Handle multi‑state, consolidated, apportionment, and nexus‑based filings.
• Review work papers and deliverables to ensure technical accuracy, compliance, and timely filing.
• Research and document complex tax issues; draft memos and provide clear guidance and solutions.
• Lead tax planning and strategic advisory services tailored to client goals and entity structures.
• Prepare estimated tax liabilities and support quarterly/annual tax strategy reviews.
• Communicate planning recommendations and insights directly with clients and coordinating professionals.
• Oversee monthly bookkeeping and financial close activities, ensuring accurate reconciliations of bank, credit card, payroll, and merchant accounts.
• Review and categorize transactions in alignment with chart of accounts, industry standards, and tax reporting requirements.
• Coordinate with bookkeeping staff to resolve variances, maintain clean general ledgers, and produce accurate financial statements for tax preparation.
• Prepare and deliver monthly financial reporting packages to clients upon completion of bookkeeping.

• Serve as the primary point of contact for a diverse portfolio of client portfolios, ensuring a high standard of service and proactive communication.
• Support client onboarding, proposal development, and engagement scoping.

• Supervise, mentor, and review work of staff and offshore preparers to ensure development and quality.
• Collaborate with bookkeeping, payroll, and advisory teams to deliver integrated client solutions.
• Contribute to ongoing process improvements and internal best practices.

• Deliver financial and tax dashboards that translate complex data into clear, actionable insights.
• Analyze results, highlight trends, and recommend strategic actions to clients and leadership.
• Support planning and decision‑making through scenario modeling, sensitivity analysis, and ROI projections.
• Produce accurate monthly and quarterly management reporting and analysis.

• Review payroll reports for accuracy, proper classifications, and compliance with federal and state wage requirements.
• Review payroll reports for completeness and proper tax with holdings across applicable states.
• Coordinate with payroll providers (e.g., Gusto, ADP, Paychex) to resolve discrepancies and maintain compliance.

• Active CPA license (required)
• Applicants must be legally authorized to work in the United States. Visa sponsorship (including H‑1B) is not available for this position.
• 6+ years of experience in public accounting or tax advisory
• Strong technical knowledge…