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.
About the Role
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.
Key Responsibilities
Tax Compliance & Technical Review
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 workpapers and deliverables to ensure technical accuracy, compliance, and timely filing
Research and document complex tax issues; draft memos and provide clear guidance and solutions
Tax Planning & Advisory
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
Bookkeeping Oversight
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
Client Relationship Management
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
Team Leadership & Workflow Management
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
Financial Reporting & Business Insights
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
Payroll Management & Compliance
Review payroll reports for accuracy, proper classifications, and compliance with federal and state wage requirements
Review payroll reports for completeness and proper tax withholdings across applicable states
Coordinate with payroll providers (e.g., Gusto, ADP, Paychex) to resolve discrepancies and maintain compliance
Qualifications
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 of federal and multi-state tax regulations
Proficiency with tax software such as Lacerte, CCH Axcess, ProConnect, or Drake
Experience with cloud-based collaboration and document management tools (i.e. Karbon)
Experience with QuickBooks (Online/Desktop), Xero, and Pilot
Experience with Gusto, ADP, SurePayroll, or other payroll systems
Demonstrated ability to manage multiple engagements and lead remote teams
Experience with offshore team oversight is a plus
Excellent organizational skills to manage multiple priorities and meet deadlines
High attention to detail and accuracy in financial and tax work
Compensation & Benefits
Competitive base salary
Fully remote work environment
401(k) Retirement Plan
Wellness Benefit: $500 annual reimbursement for qualified wellness or ergonomic home office expenses
Employer-supported medical, dental, and vision insurance options
Continuing Education Support covering required CPA CPE hours via preferred vendor
Annual performance reviews with eligibility for merit-based salary increases
Performance-based bonuses up to 20%
How to Apply
To apply, please submit your resume and a brief cover letter directly on LinkedIn.