Senior VP, ESOP Investment Banking

Stout • Chicago, IL

3d • $175,000 - $215,000

About The Position

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. The Stout ESOP Investment Banking team is seeking a Senior Vice President to lead the execution and origination of ESOP Formation, Recapitalization, and Capital Markets transactions. As a senior leader on the team, you will drive deal strategy, oversee execution teams, manage key client relationships, and meaningfully contribute to the continued growth of our ESOP Advisory practice. The ideal candidate is an accomplished investment banking professional with deep transaction experience, a strong command of complex financial modeling, and the ability to provide strategic guidance to clients, colleagues, and senior leadership. This role requires a high level of technical expertise, thought leadership, and the ability to independently manage transactions from pitch through close. You will play a central role in shaping the direction of the practice, developing junior talent, and expanding Stout’s presence in the ESOP market—supporting family- and founder-owned businesses, established ESOP companies, and dual-track transaction processes across industries.

Requirements

• 10+ years of experience in investment banking, corporate finance, private capital advisory, or related fields
• Significant experience leading and closing complex transactions; ESOP experience strongly preferred but not required
• Mastery of valuation methodologies (DCF, LBO, Comparable Companies, Precedent Transactions, Sum-of-the-Parts)
• Proven ability to guide teams in building complex financial models from scratch
• Deep experience across the deal execution lifecycle, including due diligence, structuring, modeling, negotiation, and closing
• Prior debt structuring, underwriting, or capital markets experience preferred
• Bachelor’s degree required (Finance, Economics, Mathematics, or related fields preferred); advanced degree or professional designation (MBA, CFA) is a plus
• Exceptional communication, presentation, and relationship-building skills
• Demonstrated ability to manage multiple processes simultaneously in a fast-paced environment
• High emotional intelligence, sound judgment, and strong leadership and mentorship capabilities

Responsibilities

• Lead the full lifecycle of ESOP transactions, including feasibility, structuring, valuation, modeling, financing, negotiations, and closing
• Serve as primary relationship manager for business owners, Boards of Directors, shareholders, and capital providers
• Oversee and guide Associates and Analysts in building complex three-statement financial models, valuation models, transaction scenarios, and pro forma financials
• Direct the preparation and delivery of high-impact pitch materials, management presentations, CIMs, Databooks, and other deal-related content
• Partner with sector leaders, capital markets professionals, and cross-functional teams to originate and win new mandates
• Drive strategic decision-making in live transactions, including deal structuring, lender engagement, capital raising, and negotiation of key terms
• Manage end-to-end execution activities: timelines, due diligence, data room management, financial model oversight, funds flow, and all other deal components
• Conduct and lead due diligence sessions and communicate complex technical concepts to clients in a clear, compelling manner
• Develop thought leadership and serve as a subject matter expert (SME) in the ESOP ecosystem, market trends, and transaction feasibility
• Play a critical leadership role in mentoring, developing, and evaluating junior team members
• Contribute meaningfully to strategic initiatives aimed at scaling the ESOP practice

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.
• Learn more about our benefits and commitment to your success. https://www.stout.com/en/careers/benefits

What This Job Offers

• Job Type: Full-time
• Career Level: Executive
• Number of Employees: 501-1,000 employees