Managing Director

A Chicago-based boutique investment bank is seeking a Managing Director to lead deal origination and execution within its middle-market advisory practice.

This is a senior leadership opportunity for a proven rainmaker with an established sponsor, founder, and/or corporate network who wants greater autonomy, economics, and platform support than a bulge bracket or large MM bank can offer.

• Established boutique investment bank headquartered in Chicago
• Focused on $25MM–$300MM enterprise value transactions
• Strong execution team (VP/Associate/Analyst bench in place)
• Sponsor-backed and founder-owned sell-side M&A focus
• Debt advisory and recapitalization capabilities
• Entrepreneurial culture with minimal bureaucracy

The Managing Director will:

• Originate and lead M&A and capital markets transactions
• Develop and maintain relationships with private equity firms, family offices, and strategic acquirers
• Advise founder-owned and sponsor-backed businesses on liquidity events
• Drive new business development and expand sector coverage
• Oversee deal teams through execution while maintaining senior client relationships
• Mentor junior bankers and contribute to firm strategy

This role is ideal for a senior banker seeking a more entrepreneurial environment with meaningful economics tied to production.

• 10–15+ years of investment banking experience
• Currently at Director / Managing Director level (or senior coverage banker ready to step into MD seat with production)
• Demonstrated deal origination track record
• Strong sponsor and/or corporate buyer relationships
• Experience leading sell-side M&A transactions end-to-end
• Sector expertise in Industrials, Business Services, Healthcare, Consumer, or Technology preferred