Associate/Vice President, Investment Banking - ESOP Advisory

Stout; Chicago (IL); On-site; USD 145,000 - 175,000; Full time

Job summary

Stout is hiring for an ESOP Investment Banking Senior Associate or Vice President to execute ESOP formations, recapitalizations, and related M&A work. You will collaborate with senior ESOP, Industry, and Capital Markets colleagues on live transactions and client pitches while growing your expertise in ESOP financing and transaction execution.

As part of Stout's ESOP Investment Banking Team, you will work with founders, boards, trustees, lenders, and other advisors, taking increasing ownership of

Qualifications

• 3+ years of investment banking experience.
• Advanced financial modeling and live transaction execution.
• Strong written and verbal communication.
• ESOP experience preferred.

Responsibilities

• Build and oversee three-statement financial models and transaction structures.
• Prepare pitch and execution materials for ESOP formations and capital raises.
• Lead or coordinate client meetings and present recommendations.
• Drive day-to-day transaction execution and data room management.
• Lead due diligence sessions and liaise with lenders and trustees.
• Develop expertise in ESOP transaction ecosystem.

Skills

Investment banking

Financial modeling

ESOP

Valuation

Client management

Leadership

Project management

Education

Bachelor's degree

Tools

Excel

PowerPoint

Word

Job description

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 a Senior 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 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

The 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 $145,000 - $175,000 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.