JOBSEARCHER

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

StoutChicago, ILApril 12th, 2026
At Stout, we’re dedicated to exceeding expectations in all we do – we call it Relentless Excellence ®. Both our client service and culture are second to none, stemming from our firmwide embrace of our core values: Positive and Team-Oriented, Accountable, Committed, Relationship-Focused, Super-Responsive, and being Great communicators. Sound like a place you can grow and succeed? Read on to learn more about an exciting opportunity to join our team.Impact You’ll MakeAs 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.What You'll DoLead multiple tax due diligence & structuring engagements simultaneously, effectively managing competing prioritiesIdentify key tax risks, exposures, and potential deal breakers that materially impact transaction valueAnalyze complex federal, state, and international tax positions, including historical filings, deferred tax assets/liabilities, and uncertain tax positionsPrepare clear, concise, and thorough due diligence reports and presentations for clients and deal teamsConduct calls and meetings with client management, target company teams, and advisors to discuss findingsReview and interpret purchase agreements, tax indemnities, and other deal documents to provide actionable insightsCollaborate with financial diligence and quality of earnings team to understand financial implications of tax positionsIdentify 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 leadershipParticipate in recruiting, training, and development of junior team membersWhat You BringSolid understanding of M&A transaction structures, due diligence processes, and purchase agreement implicationsExceptional analytical, technical, and problem-solving skills, with meticulous attention to detailExcellent verbal and written communication skills; able to translate complex tax issues into actionable insightsStrong relationship-building skills; collaborative and client-focusedEntrepreneurial mindset with proactive approach to work and challengesSelf-motivated, accountable, and able to manage multiple priorities effectivelyAdvanced proficiency in Excel and PowerPointInterest in learning and utilizing new technology, including AI, to perform more efficient and better quality workAbility to thrive in a fast-paced, evolving environmentWillingness to travel up to 25% on short noticeEducation and/or Training:CPA or JD requiredTax LLM preferred, with deep knowledge of U.S. federal, state, and international tax laws and regulationsMinimum 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 diligenceBig Four or similar experience strongly preferredHow You’ll ThriveEmbrace an entrepreneurial mindset in a rapidly-growing teamComfort with ever-changing client-imposed deadlines with flexibility and adaptabilityExhibit strong organizational skills to manage competing priorities effectivelyCollaborate with engagement leaders and team members while embodying Stout’s core values: Positive and Team-Oriented, Accountable, Committed, Relationship-Focused, Super-Responsive, and being Great communicatorsDemonstrate a commitment to delivering Relentless Excellence® in client service and team collaborationWhy Stout?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.Learn more about our benefits and commitment to your success.https://www.stout.com/en/careers/benefitsThe specific statements shown in each section of this description are not intended to be all-inclusive. They represent typical elements and criteria necessary to successfully perform the job.Stout is an Equal Employment Opportunity. All qualified applicants will receive consideration for employment on the basis of valid job requirements, qualifications and merit without regard to race, color, religion, sex, national origin, disability, age, protected veteran status or any other characteristic protected by applicable local, state or federal law. Stout is required by applicable state and local laws to include a reasonable estimate of the compensation range for this role. The range for this role considers several factors including but not limited to prior work and industry experience, education level, and unique skills. The disclosed range estimate has not been adjusted for any applicable geographic differential associated with the location at which the position may be filled. It is not typical for an individual to be hired at or near the top of the range for their role and compensation decisions are dependent on the facts and circumstances of each case.A reasonable estimate of the current range is $87,000.00 - $195,000.00 Annual. This role is also anticipated to be eligible to participate in an annual bonus plan. Information about benefits can be found here - https://www.stout.com/en/careers/benefits.