Investment Banking Managing Director (lower middle market)

Prospect Rock Partners • Chicago, IL

2d • $250,000

About The Position

Our client, a leading lower middle-market investment bank, is dedicated to serving founder-owned, family-owned, and privately held businesses. The firm provides strategic M&A advisory, capital raising, and financial advisory services across a range of industries, with a reputation for deep client relationships, entrepreneurial thinking, and exceptional execution. As the firm's Technology practice continues to expand, the firm is seeking an experienced Managing Director to help grow its technology franchise by originating and executing transactions across software, tech-enabled services, IT services, digital infrastructure, cybersecurity, and related technology sectors. The Managing Director will be responsible for driving the growth of the Technology Investment Banking practice through proactive business development, client relationship management, and transaction leadership. This individual will originate new advisory mandates, cultivate long-term relationships with founders, business owners, private equity sponsors, and strategic acquirers, and lead transactions from initial engagement through closing. This role is best suited for an entrepreneurial investment banker with a proven history of generating revenue, developing trusted client relationships, and successfully advising middle-market technology companies on strategic transactions.

Requirements

• 10+ years of investment banking experience with a strong focus on Technology M&A.
• Demonstrated track record of originating and closing middle-market M&A transactions.
• Existing network of founders, entrepreneurs, private equity firms, and strategic acquirers within the technology sector.
• Proven ability to independently source and win new advisory engagements.
• Strong understanding of software, tech-enabled services, IT services, cybersecurity, digital infrastructure, and related technology markets.
• Excellent leadership, communication, negotiation, and relationship management skills.
• Bachelor's degree required.

Nice To Haves

• MBA or other advanced degree is a plus.
• An established reputation in the middle market and a demonstrated ability to generate meaningful advisory revenue through long-standing client relationships and referral networks.
• Bring an active network of technology founders, executives, investors, and private equity sponsors.
• Develop a sustainable pipeline capable of producing multiple new advisory mandates annually.
• Partner closely with other senior bankers to pursue cross-sector opportunities and maximize firm-wide relationships.
• Contribute meaningfully to the long-term expansion and market positioning of the Technology practice.

Responsibilities

• Develop and execute a business development strategy to expand the Technology practice.
• Generate a consistent pipeline of new M&A and capital advisory opportunities through proactive outreach, referrals, and industry relationships.
• Build and maintain trusted relationships with founders, CEOs, shareholders, private equity firms, family offices, and strategic buyers.
• Represent the firm at industry conferences, networking events, and thought leadership initiatives to enhance the firm's market presence.
• Collaborate with senior leadership to identify cross-selling opportunities across sectors and service lines.
• Consistently meet or exceed annual business development and revenue generation objectives.
• Lead sell-side, buy-side, recapitalization, and capital raising engagements for middle-market technology companies.
• Serve as the senior client advisor throughout all phases of a transaction.
• Oversee valuation analysis, marketing materials, negotiations, due diligence, and transaction execution.
• Coordinate internal deal teams while ensuring exceptional client service and execution quality.
• Mentor, develop, and recruit junior investment banking professionals.
• Foster a collaborative, high-performance culture focused on client success and professional development.
• Help shape the strategic direction and continued growth of the Technology practice.

Benefits

• Competitive compensation with meaningful upside tied to business development, transaction execution, and long-term practice growth.
• Base is 250k non-negotiable; upside in the splits.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior