Vice President, Transaction Advisory (M&A Tax Services)

Stout Risius Ross • Chicago, IL

1d • $87,000 - $195,000

About The Position

As a full-time Vice President or Senior Vice President in our rapidly-growing M&A Tax Services practice, you will play a pivotal role in shaping the outcomes of complex, high-stakes transactions. By leading buy-side and sell-side tax due diligence & transaction structuring engagements for private equity and corporate clients, you provide critical insights that directly inform investment decisions, negotiation strategies, and deal structures. Your analysis of historical and projected tax positions, review of key contractual obligations, and evaluation of tax risks and opportunities ensures clients have the clarity and confidence they need to execute transactions successfully. Partnering closely with deal teams, management, investment bankers, legal counsel, and other external advisors, you drive actionable insights that enhance deal value and mitigate risk across the transaction lifecycle.

Requirements

• Solid understanding of M&A transaction structures, due diligence processes, and purchase agreement implications
• Exceptional analytical, technical, and problem-solving skills, with meticulous attention to detail
• Excellent verbal and written communication skills; able to translate complex tax issues into actionable insights
• Strong relationship-building skills; collaborative and client-focused
• Entrepreneurial mindset with proactive approach to work and challenges
• Self-motivated, accountable, and able to manage multiple priorities effectively
• Advanced proficiency in Excel and PowerPoint
• Interest in learning and utilizing new technology, including AI, to perform more efficient and better quality work
• Ability to thrive in a fast-paced, evolving environment
• Willingness to travel up to 25% on short notice
• CPA or JD required
• Minimum of 3–7 years of experience in tax-related consulting and compliance, including at least 3-5 years specifically in M&A tax deal work or tax due diligence

Nice To Haves

• Tax LLM preferred, with deep knowledge of U.S. federal, state, and international tax laws and regulations
• Big Four or similar experience strongly preferred

Responsibilities

• Lead multiple tax due diligence & structuring engagements simultaneously, effectively managing competing priorities
• Identify key tax risks, exposures, and potential deal breakers that materially impact transaction value
• Analyze complex federal, state, and international tax positions, including historical filings, deferred tax assets/liabilities, and uncertain tax positions
• Prepare clear, concise, and thorough due diligence reports and presentations for clients and deal teams
• Conduct calls and meetings with client management, target company teams, and advisors to discuss findings
• Review and interpret purchase agreements, tax indemnities, and other deal documents to provide actionable insights
• Collaborate with financial diligence and quality of earnings team to understand financial implications of tax positions
• Identify opportunities to cross-sell services and articulate to other verticals how they can utilize M&A Tax Services for their clients.
• Contribute to business development initiatives, including client proposals and thought leadership
• Participate in recruiting, training, and development of junior team members

Benefits

• At Stout, we offer a comprehensive Total Rewards program with competitive compensation, benefits, and wellness options tailored to support employees at every stage of life.
• We foster a culture of inclusion and respect, embracing diverse perspectives and experiences to drive innovation and success.
• Our leadership is committed to inclusion and belonging across the organization and in the communities we serve.
• We invest in professional growth through ongoing training, mentorship, employee resource groups, and clear performance feedback, ensuring our employees are supported in achieving their career goals.
• Stout provides flexible work schedules and a discretionary time off policy to promote work-life balance and help employees lead fulfilling lives.

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: Ph.D. or professional degree