Outlook Tax & Advisory · 2 months ago
Remote Tax Manager
United States
Full-time
Remote
Senior Level
6+ years expOutlook Accounting & Taxes Corporation is a leading accounting and consulting firm based in the Chicagoland area, focused on helping clients achieve financial freedom. The Tax Manager will oversee tax compliance and consulting services, manage client relationships, and lead a team to ensure operational excellence.
Accounting
No H1B
Responsibilities
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
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 withholdings across applicable states
Coordinate with payroll providers (e.g., Gusto, ADP, Paychex) to resolve discrepancies and maintain compliance
Qualification
Required
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
Excellent organizational skills to manage multiple priorities and meet deadlines
High attention to detail and accuracy in financial and tax work
Preferred
Experience with offshore team oversight is a plus
Benefits
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%
Company
Outlook Tax & Advisory
Outlook Tax & Advisory is a modern tax, accounting, and financial advisory firm helping individuals and middle-market businesses achieve clarity, confidence, and continuity in their financial operations.
51-200 employees
Funding
Current Stage
Growth StageCompany data provided by crunchbase