Managing Director, Middle Market Investment Banking

Location: Chicago, IL; Milwaukee, WI; or Remote within the United States

Expected salary: $300,000 annually, based on experience, qualifications, and location. Additional incentive compensation may apply.

Company

CIBC is a North American financial institution providing advisory, financing, capital markets, and treasury services to corporate, government, institutional, and individual clients.

What you will do

• Originate and convert new opportunities, secure fee-paying engagements, and expand relationships with private equity sponsors, entrepreneurs, companies, and market influencers.
• Lead vertical-market strategy by translating industry and market trends into actionable advice and thought leadership.
• Oversee middle-market M&A and financing mandates from pitch through closing, including onboarding, AML clearance, financial modeling, analysis, and stakeholder coordination.
• Partner with product and industry experts across Capital Markets and CIBC Bank USA while maintaining business-development and transaction activity in Salesforce.
• Build and develop inclusive, high-performing deal teams through mentorship, coaching, teaching, and feedback.
• Ensure advice and execution comply with applicable laws, regulations, company policies, and professional standards.

Requirements

• At least 10 years of relevant investment banking experience, including transaction origination, execution, client coverage, and team leadership at Managing Director or equivalent level.
• Deep expertise in middle-market M&A, transaction processes, valuation, financial analysis, and market dynamics.
• Established relationships and sector expertise in Business Services, Consumer, Healthcare Products, or Software and Technology.
• Demonstrated ability to generate ideas, solve complex client challenges, win mandates, and communicate recommendations to senior executives, boards, investors, and stakeholders.
• Proven relationship leadership, sound judgment under pressure, professional integrity, and team-management ability.
• Must be legally eligible to work at the specified U.S. locations; employment visa sponsorship is not available.

Culture & Benefits

• Full-time regular employment with a 40-hour work week.
• Medical, dental, vision, health savings account, life, disability, and other insurance plans.
• Paid sick leave, parental leave, vacation, holidays, and 401(k).
• Competitive salary, incentive pay, banking benefits, wellbeing support, and recognition programs.
• Professional growth initiatives, including a paid Purpose Day for development and personal growth.
• Inclusive workplace with accessible candidate accommodations and opportunities for flexible remote work.

Hiring process

• The process may include an attribute-based assessment and skills tests such as simulations, coding, or Microsoft Office evaluations.