Senior Tax Manager in Chicago, Illinois

Senior Tax Manager

Outlook Tax & Advisory is a growing accounting and advisory firm serving small and mid-sized businesses across the U.S. We file roughly 1,500 returns per year across individuals, S-corps, partnerships, C-corps, non-profits, and trusts. Beyond compliance, we provide ongoing tax planning, strategy, and advisory work, quarterly reviews, year-end planning, and transaction support, for clients who want a real tax partner rather than just a preparer.

Our production is supported by an offshore preparation and review team; our U.S.

-based leadership owns final review, client relationships, and quality standards. We are hiring a Senior Tax Manager to own technical review and quality across the practice. This is an opportunity for someone who enjoys solving complex tax issues and serving as the firm's technical authority while helping mentor and develop a growing team of tax professionals. This is the role for a senior tax professional who wants both technical depth and direct client work, leading complex reviews during busy season and owning strategic planning and advisory work year-round.

As our practice continues to expand, this individual will play a key role in shaping our tax department, building technical capabilities, and establishing best practices across the firm.

You'll personally review ~30% of our returns that need senior eyes: complex corporate filings, multi-state and consolidated returns, partnerships with tricky allocations, high-net-worth individuals, trusts, and anything our offshore team flags for escalation. For the remaining ~70%, you'll oversee the offshore review process: spot-checking sampled returns, calibrating the offshore senior reviewer, refining checklists and review standards, and catching systemic issues before they become filing problems.

You'll lead tax planning and advisory work directly with our higher-tier clients. That includes quarterly tax strategy reviews, year-end planning, transaction-driven work (entity restructuring, M&A, real estate, R&D credits, retirement plan design), and reactive advisory on whatever clients bring to you. You'll work with a small U.S. team (2-3 direct reports) and coordinate closely with the offshore production team. Your North Star: every return we file is technically correct and on time;

every client conversation leaves them better-informed and better positioned.

• Direct review
• Review approximately 30% of all returns (~450/year, concentrated in busy season), focused on complex 1120, 1120S, 1065, 1041, 990, and multi-state individual returns
• Sign and file returns under your CPA license where appropriate
• Document review notes, technical positions, and decisions for the file

• Offshore quality oversight
• Spot-check sampled returns from offshore senior reviewer's queue (target 10-15% sampling rate)
• Provide structured feedback to offshore senior reviewer; calibrate review standards regularly
• Identify systemic preparation issues and partner with offshore team lead to address them
• Maintain and evolve the firm's review checklist, technical position library, and quality standards

• Tax planning and advisory
• Lead quarterly tax strategy reviews with a defined book of advisory clients
• Run year-end planning engagements: scenario modeling, deferral/acceleration strategies, retirement plan design, estimated tax adjustments
• Handle transaction-driven work as it comes up: entity restructuring, M&A tax support, real estate transactions, R&D credit studies, cost segregation
• Serve as the named tax advisor for higher-tier clients. They call you with questions, you own the relationship
• Document planning decisions and positions clearly so they survive into future returns

• Team support and development
• Lead 2-3 U.S.
  
  -based direct reports (senior staff and reviewers)
• Provide technical guidance and training across the broader team
• Handle escalations from offshore preparers and U.S. staff on complex technical issues

• Practice contribution
• Research and document positions on complex tax issues; draft technical memos
• Stay current on federal and multi-state tax law changes; communicate relevant updates internally
• Contribute to process improvements,…