Associate/Vice President, Investment Banking - ESOP Advisory

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 Make

The Stout ESOP Investment Banking Team is seeking an Associate or Vice President to play a central role in executing ESOP formation, recapitalization, and related M&A transactions. You will work directly with senior ESOP, Industry and Capital Markets colleagues across live transactions, pitches, and business development initiatives. The role combines the technical rigor of traditional investment banking with differentiated exposure to ESOP structuring and financing. Successful candidates will bring strong technical & complex financial modeling capabilities, detail-oriented drive, intellectual curiosity and sound judgment to take increasing ownership of transaction execution based on experience and level.

As a member of Stout’s ESOP Investment Banking Team, you will gain significant exposure to founders, shareholders, Boards, trustees, lenders, and other transaction advisors while developing a broad skill set across M&A, valuation, capital structure, debt financing, and ESOP-specific execution. Associates will own meaningful analytical and execution workstreams. Vice Presidents will be expected to lead major workstreams, manage junior team members, and serve as a day-to-day point of contact for clients and counterparties.

The ESOP Investment Banking Team advises successful family- and founder-owned businesses evaluating monetization alternatives, including an ESOP and more traditional sale alternatives. In most engagements, Stout serves as the sole financial advisor, evaluating feasibility and transaction alternatives, structuring and executing the ESOP transaction, and coordinating the related financing, often with a capital raise led by Stout’s Capital Markets Team.

We also work with Industry bankers, Capital Markets colleagues, and other Stout business lines to identify owners for whom an ESOP may be a compelling alternative, including dual-track situations that compare ESOP and traditional M&A outcomes. For established ESOP-owned companies, we advise on recapitalizations, refinancings, liquidity and repurchase obligation planning, and strategic M&A, including sales to strategic buyers or private equity firms.

What You’ll Do

Build and oversee integrated three-statement financial models, valuation analyses, transaction models, and pro forma capital structures, including detailed transaction adjustments and debt schedules

Prepare pitch and execution materials for ESOP formations, recapitalizations, capital raises, and strategic alternatives, working with practice leaders, industry bankers, and the Capital Markets Team to win and execute new mandates

Participate in client meetings and based on experience and level, present analyses and transaction recommendations directly to business owners, management teams, Boards, and other senior stakeholders

Perform detailed financial modeling, valuation, transaction structuring, and financing analysis for live ESOP transactions; evaluate alternatives and support negotiations with clients, trustees, lenders, and other counterparties

Drive day-to-day transaction execution, including managing timelines, coordinating information requests and data rooms, updating financial models, preparing CIMs and Databooks, developing Board and shareholder materials, coordinating financing workstreams and lender materials, and supporting funds flow and closing activities

Lead or participate in due diligence sessions with clients, lenders, trustees, legal and tax advisors, and other transaction counterparties

Conduct company, industry, credit, economic, and market research to support valuation, capital structure, financing, and client recommendations

Communicate effectively with key stakeholders, including business owners, shareholders, Boards, trustees, financial institutions, legal and tax advisors, and other transaction participants

Develop deep expertise in the ESOP transaction ecosystem, including feasibility, valuation, structuring, financing, trustee processes, recapitalizations, and closing mechanics

Take a leadership role commensurate with experience. Vice Presidents will be expected to lead major internal and external workstreams, review junior team output, and help develop junior bankers

Leverage AI-enabled tools and emerging technologies to enhance research, streamline deliverable preparation, and improve overall efficiency and insight

What You Bring

At least 3 years of investment banking experience. Title and level will be based on relevant experience, transaction exposure, and demonstrated capabilities

Advanced technical and financial modeling skills, with experience supporting or leading live transaction execution

ESOP experience is preferred but not required. Candidates with strong M&A, leveraged finance, or capital markets backgrounds who are interested in developing ESOP expertise are encouraged to apply

Ability to perform valuation analyses, including Discounted Cash Flow, Leveraged Buyout, Comparable Companies, Precedent Transactions, and Sum-of-the-Parts analyses, as relevant

Demonstrated ability to build complex financial models from scratch, including integrated three-statement and transaction models

Experience across the end-to-end deal execution lifecycle, with the ability to independently manage workstreams commensurate with experience and level

Debt structuring, leveraged finance, or underwriting experience is a plus but not required

Bachelor’s degree required

Advanced proficiency in Excel, PowerPoint, and Word

Familiarity with or interest in using AI-enabled tools to improve productivity, research, analysis, and preparation of client materials

Strong written and verbal communication skills, sound judgment, intellectual curiosity, and the ability to perform at a high level in a demanding, collaborative deal environment

For Vice President-level candidates, demonstrated experience leading multiple transaction workstreams, managing and reviewing junior team members, and interacting directly with senior clients and transaction counterparties is strongly preferred

Must be authorized to work in the United States without current or future employer sponsorship

How You’ll Thrive

Take ownership of your workstreams, stay close to the details, exercise sound judgment, and consistently deliver high-quality results

Communicate clearly and respond promptly to clients, senior bankers, colleagues, and transaction participants

Build trusted relationships through preparation, responsiveness, sound judgment, and consistent execution

Help develop junior team members while continuing to strengthen your own technical, sector, transaction, and client-facing capabilities

Understand the broader transaction objectives and trade-offs, not only the individual analysis, and anticipate issues before they affect execution

Embody Stout’s core values by being Positive and Team-Oriented, Accountable, Committed, Entrepreneurial, Relationship-Focused, Super-Responsive, and a Great Communicator

Deliver Relentless Excellence® through disciplined execution, strong client service, and a commitment to the quality of your work and the experience of your colleagues

• Why 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 leadershi