Transaction Director, Middle Market Team (M&A)

Benchmark International is seeking an experienced and dynamic Transaction Director (TD) to lead our Sell side Middle Market Team. This senior-level role will involve building out our world class transaction team and overseeing the transaction execution function for this key market segment. In the role, the successful candidate, in partnership with the Managing Director, will build and maintain relationships with clients, and lead a team of professionals in providing world-class advisory services to our middle-market clients. The ideal candidate will be a player coach with a proven track record of executing sell side, Middle Market M&A deals, exceptional team building and leadership capabilities, and a deep understanding of the complexities of Middle Market transactions. The TD reports directly to the Managing Director.

Key Responsibilities

• Lead Deal Team: Direct and lead the execution function of the M&A life cycle. The focus will be on running the Middle Market Team, driving transactions from client engagement through deal closing, including due diligence, negotiation, structuring, and closing. Provide high-level strategic advice to clients, ensuring alignment with their objectives.
• Client Relationship Management: Develop and maintain strong relationships with key stakeholders at client companies. Act as a trusted advisor, providing insights into market trends, potential opportunities, and the strategic implications of transactions.
• Team Construction, Leadership & Development: Manage and mentor a high-performing team of senior bankers, associates, and analysts. Foster a collaborative and results-oriented environment while ensuring the continued professional development of team members.
• Deal Origination & Execution: While the Middle Market Team has a dedicated Deal Origination team, the TD, working in tandem with the MD, will play a key role
• assisting their origination counterpart in sourcing new M&A mandates. Oversee and manage the execution of transactions from onboarding through to completion.
• Strategic Planning & Market Intelligence: Stay ahead of industry trends and market dynamics to provide clients with actionable insights. Drive the development of thought leadership content and occasionally represent the firm at industry conferences, professional speaking opportunities, panels, etc.
• Risk Management & Compliance: Ensure all transactions adhere to legal, regulatory, and internal risk management protocols. Oversee due diligence processes and coordinate with legal, financial, and tax advisors to ensure the successful closure of deals.
• Financial Analysis: Oversee the financial analysis processes for M&A transactions. Provide insights into financial structuring and the overall strategic impact of transactions.

Job Requirements

As leader of the Middle Market Team, the TD will be one of the faces of Benchmark International and as such will have additional responsibilities to corporate as required.

• Be capable of handling setbacks, having difficult conversations with business owners, negotiating against veteran professional acquirers, taking responsibility for process breakdowns even when not responsible, and fostering cooperation with client’s attorneys and accountants.
• Consistently present themselves in a professional manner in keeping with Benchmark International’s image (as shown, for example, on the company’s website).
• Work outside normal business hours at times, whether early or late, as required by client schedules and expectations.
• Be available to travel for occasional overnight trips on short notice (rarely, if ever, longer than three days).
• Ability to obtain a Florida real-estate sales associate license within 90 days of employment.
• Have no unfavorable history with FINRA, the SEC, or any state regulatory agency.

Specific Qualifications

• Experience: Minimum 10 years of experience in M&A advisory, with a strong track record in managing large deal teams and complex transactions across multiple industries.
• Education: A Bachelor's degree in Finance, Economics, Business, or related field; an MBA or equivalent advanced degree is preferred. JD a plus.
• Leadership: Proven ability to recruit, lead, develop, and inspire teams, with a hands-on approach to mentoring and developing talent within the organization.
• Client-Facing Expertise: Exceptional client relationship skills, with a clear history of successfully originating and executing middle market M&A transactions.
• Technical Skills: Strong financial acumen, including advanced financial modeling, valuation techniques, and understanding of deal structures, legal deal documentation and structures, and M&A tax.
• Industry Knowledge: Deep understanding of M&A markets and trends, knowledge of diverse industries and business models and a broad network of relationships across the M&A ecosystem.
• Communication Skills: Superior verbal and written communication skills, with the ability to present complex ideas clearly and persuasively to stakeholders, the deal team, and Benchmark International leadership.

Personal Attributes

• Process Driven: Driving the team and deals through process. Strict adherence to the Benchmark International process manual.
• Strategic Thinker: Able to view the big picture and anticipate long-term implications for clients and the firm.
• Results-Oriented: Strong focus on delivering results and achieving success in a fast-paced, high-pressure environment.
• Entrepreneurial Mindset: Brings a startup mentality. Proactive in seeking new business opportunities and delivering innovative solutions to clients.
• Integrity and Professionalism: Uphold the highest standards of ethical behavior and professionalism in all aspects of work.

Compensation

This is a senior leadership position offering a competitive compensation package, including base salary and performance-based bonuses. Salary range for this position is $150,000 to $200,000 with on target earnings in excess of $350,000.

Benefits

All Benchmark International positions offer paid time off, standard 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 accounts; and flexible dependent care assistance accounts.

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 passions 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 sale of mid-market companies, our transaction 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.

Unfortunately, Benchmark International is not in a position to sponsor visas for candidates at this time.

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.

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