Senior Investment Banker, Head of Middle Market M&A

Benchmark International’s U.S. mergers & acquisitions practice is seeking a highly accomplished Senior Investment Banker to serve as Head of Middle Market M&A. This key leadership role oversees our national Middle Market sell-side practice, representing owner-operated companies across the United States generating $10–$25 million in EBITDA.

You will lead a world-class transaction execution team, deliver strategic advisory services to founder-led businesses, and manage a sophisticated portfolio of sell-side engagements from initial client onboarding through to a successful closing. As a senior leader and visible face of the firm, you will collaborate closely with Benchmark International’s CEO and executive leadership team.

This position requires a seasoned dealmaker with a strong sell-side execution background, superior leadership skills, and the ability to mentor and inspire high-performing bankers. The role is ideal for a player-coach who excels at navigating complex middle market transactions and driving transformational outcomes for business owners.

Job Responsibilities:

Lead Deal Team & M&A Execution
• Direct and lead the full execution function of the M&A lifecycle for Middle Market engagements.
• Oversee active portfolio management and drive transactions through due diligence, negotiation, structuring, and closing.
• Provide high-level strategic guidance to clients, ensuring alignment with their goals and market realities.
• Ensure rigorous adherence to Benchmark International’s process manual and best-in-class execution standards.
Client Relationship Management
• Build and maintain strong relationships with owner-operators and executive teams.
• Serve as a trusted advisor, offering insight into market trends, valuation dynamics, buyer behavior, and strategic alternatives.
• Support clients through the emotional and strategic complexities of selling a business.
Team Construction, Leadership & Development
• Recruit, develop, and lead a high-performing team of senior bankers, associates, and analysts.
• Foster a collaborative, accountable, results-oriented environment.
• Mentor team members to enhance their technical skills, client communication, and deal leadership abilities.
Deal Origination Support
• Collaborate with the Middle Market Team’s dedicated Origination Unit to assist in sourcing new M&A mandates.
• Leverage your experience and credibility to support origination strategy and win new client engagements.
Strategic Planning & Market Intelligence
• Remain current on industry, economic, and M&A market trends.
• Translate market dynamics into actionable insights for clients and internal teams.
• Represent Benchmark International at industry conferences, speaking events, and professional forums.
Risk Management & Compliance
• Ensure all transactions comply with legal, regulatory, and internal risk management standards.
• Oversee due diligence processes and coordinate with legal, financial, and tax advisors.
• Proactively identify risks and ensure smooth execution across every stage.
Financial Analysis Oversight
• Supervise financial modeling, valuation assessments, strategic analysis, and deal structuring.
• Provide senior-level review and guidance to support accurate, effective financial decision-making.

Additional Leadership Expectations

As the leader and face of the Middle Market Team, you will:
• Handle setbacks professionally and confidently.
• Lead difficult conversations with owners, acquirers, and advisors.
• Negotiate against seasoned professional buyers.
• Take responsibility for process breakdowns, even when not directly responsible.
• Foster cooperation with clients’ attorneys, accountants, and other advisors.
• Always Maintain Benchmark International’s professional image.
• Work outside normal business hours when required to meet client expectations.
• Be available for occasional short notice travel (rarely more than three days).

Job Qualifications:

Experience
• Minimum 12 years of M&A advisory experience with a proven track record executing complex middle-market sell-side transactions across industries.
• Demonstrated ability to manage large deal teams and multiple simultaneous assignments.
Education
• Bachelor’s degree in Finance, Economics, Business, or related field required.
• MBA or advanced degree preferred; JD a plus.
Leadership Skills
• Proven ability to recruit, lead, and inspire high-performing teams.
• Hands-on leader committed to developing talent.
Client-Facing Expertise
• Exceptional client relationship and advisory skills.
• Clear history of successfully originating and executing middle market M&A engagements.
Technical Competence
• Strong financial modeling, valuation, and transaction structuring skills.
• Deep understanding of legal documentation, deal mechanics, and M&A tax considerations.
Industry Knowledge
• Broad-based understanding of M&A markets, buyer landscapes, and industry-specific deal dynamics.
• Extensive professional network within the M&A ecosystem.
Communication Skills
• Superior verbal and written communication skills.
• Ability to distill complex ideas into clear, actionable insight.

Personal Attributes
• Process Driven: Strong adherence to Benchmark International’s established M&A processes.
• Strategic Thinker: Capable of seeing the big picture and anticipating long-term implications.
• Results-Oriented: Operates effectively in fast-paced, high-pressure deal environments.
• Entrepreneurial Mindset: Proactive, innovative, and opportunity focused.
• Integrity & Professionalism: Upholds the highest ethical standards.

Additional requirements:
• Ability to obtain a Florida real-estate sales associate license within 90 days of employment.
• No unfavorable history with FINRA, the SEC, or any state regulatory agency.
• Ability to pass a criminal and professional background check prior to starting date.
• Interested candidates should submit a resume and cover letter outlining their qualifications and relevant experience,

Compensation

This senior leadership role offers a competitive compensation package, including a base salary, commission, and performance-based bonuses. Final package will be determined on qualifications and experience.

Benefits

All Benchmark International positions offer paid time off, standard holidays, birthday holidays, and community service days. Employees are eligible for highly competitive company-subsidized medical, dental, vision, and AD&D insurance; 401k with company matching; flexible spending and health savings accounts (FSA & HSA); and flexible dependent care assistance accounts.

Relocation assistance is not available for this role.

Social Responsibility

Benchmark International is an active, contributing member of the communities in which we work. The company participates in significant charitable giving opportunities throughout the year. Many of the recipient charities have been identified by our individual employees because of their personal passion for supporting particular needs. In addition, each employee is encouraged to use two paid workdays per year to provide their labor and skills to the community.

About Benchmark International

Benchmark International is a global mergers and acquisitions firm dedicated to delivering creative, value-maximizing solutions for business owners seeking to grow or exit their companies. Recognized as the #1 Sell-side Privately Owned M&A Advisor in the World by PitchBook and Refinitiv and named Investment Banking Firm of the Year by both the M&A Advisor and the Global M&A Network, we are known for our award-winning process and world-class service.

Specializing in the transaction of mid-market companies, our teams operate from offices across the globe, representing clients in a wide variety of industries. Our unique, technology-driven approach connects sellers with the right acquirers—whether local or international—through a combination of proprietary databases, deep market insight, and strategic outreach.

We offer an exciting opportunity to be part of a high-performance team with global reach. Our culture is rooted in collaboration, innovation, and continuous growth. We believe in promoting from within and are actively looking for ambitious professionals ready to shape the next chapter of our success story.

Join us and be part of the next generation of leaders redefining M&A excellence.

Benchmark International provides equal employment opportunities to all qualified individuals without regard to race, color, religion, sex, gender identity, sexual orientation, pregnancy, age, national origin, physical or mental disability, military or veteran status, genetic information, or any other protected classification. Equal employment opportunity includes, but is not limited to, hiring, training, promotion, demotion, transfer, leaves of absence, and termination. The company takes allegations of discrimination, harassment, and retaliation seriously, and will promptly investigate when such behavior is reported.