Managing Director - Debt & Structured Finance

About CastleSquare:

CastleSquare is an emerging advisory firm specializing in structured finance, providing customized capital solutions for our clients. We pride ourselves on delivering exceptional execution through our deep industry expertise, strong lender relationships, and cutting-edge technology. Our firm has a fun entrepreneurial culture that supports its professionals with comprehensive back-office assistance, allowing them to focus on business development and deal execution.

Position Overview:

CastleSquare is seeking a highly experienced and results-driven Managing Director to join our Structured Finance group. This position is based in Miami, Florida, and will be focused on originating and financing deals throughout South Florida. The ideal candidate has a proven track record of originating and closing at least 5 to 10 exclusive senior debt mandates per year, with a strong portfolio of repeat, loyal clients. We are looking for a dynamic leader who excels in structured finance, has an extensive network of industry relationships, and is committed to working exclusively on mandated transactions.

Key Responsibilities:

Originate, structure, and close commercial real estate financing transactions, including senior debt, mezzanine financing, and preferred equity solutions.

Identify transaction strengths and potential risks.

Develop and maintain long-term relationships with developers, owners, and institutional investors to secure repeat business.

Execute exclusive financing mandates, ensuring clients receive superior execution tailored to their capital needs and a controlled process it run.

Leverage CastleSquare’s technology and back-office support to maximize efficiency, deal flow, and closings.

Leverage firm software to deliver optimal financing solutions for clients.

Stay informed on market trends, capital sources, and financial products to maintain a competitive edge.

Represent CastleSquare at industry conferences, networking events, social media, and client meetings to enhance market presence.

Qualifications & Experience:

Minimum 5 years of experience in commercial real estate finance, capital markets, or structured debt placement.

Proven track record of successfully originating and closing a high volume of exclusive senior debt transactions annually.

Strong relationships with lenders, private equity firms, institutional investors, and other capital providers.

Ability to transfer and grow an existing book of business within CastleSquare’s platform.

Deep understanding of structured finance products, credit analysis, and risk assessment.

Excellent negotiation, presentation, and client management skills.

Highly motivated, self-driven professional with a strong entrepreneurial mindset.

Why Join CastleSquare?

Fun entrepreneurial culture that fosters innovation and rewards initiative.

Exclusive mandate model ensuring high-quality transactions, client trust, and controlled processes in the capital markets.

Comprehensive back-office support, allowing you to focus on deal-making and client relationships.

Cutting-edge technology to streamline deal execution and enhance productivity.

Competitive compensation structure based on performance.

If you are a top-performing capital markets intermediary seeking a highly rewarding, client-focused role at a more nimble and entrepreneurial firm, we invite you to apply to CastleSquare’s Managing Director – Structured Finance position today.