Senior Investment Banker, Head of Middle Market M&A

Benchmark International • Tampa, FL

43d

About The Position

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.

Requirements

• 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.
• Bachelor's degree in Finance, Economics, Business, or related field required.
• Proven ability to recruit, lead, and inspire high-performing teams.
• Hands-on leader committed to developing talent.
• Exceptional client relationship and advisory skills.
• Clear history of successfully originating and executing middle market M&A engagements.
• Strong financial modeling, valuation, and transaction structuring skills.
• Deep understanding of legal documentation, deal mechanics, and M&A tax considerations.
• Broad-based understanding of M&A markets, buyer landscapes, and industry-specific deal dynamics.
• Extensive professional network within the M&A ecosystem.
• Superior verbal and written communication skills.
• Ability to distill complex ideas into clear, actionable insight.
• 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.
• 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.

Nice To Haves

• MBA or advanced degree preferred; JD a plus.

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.

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.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Industry: Professional, Scientific, and Technical Services