Managing Director/COO- Miami, FL at The Calendar Group – Miami, Florida

Our client is seeking a Managing Director/COO to serve as a true operating partner to the Founder/CEO of a Miami-based ultra-luxury real estate investment and development platform, spanning development, brokerage, and capital markets. This individual will own deal execution, revenue generation, and pipeline management, ensuring consistent progression of the firm’s highest-value opportunities.
Key Responsibilities

• Act as a strategic partner to the Founder, supporting decision-making and execution across business priorities
• Own and manage the firm’s deal pipeline, ensuring consistent progression of the firm’s highest-value opportunities from sourcing through close.
• Lead deal execution across development, brokerage, and capital markets initiatives.
• Drive revenue generation by identifying, advancing, and closing high-value opportunities.
• Build and maintain relationships with investors, family offices, developers, brokers, and key stakeholders.
• Identify opportunities across the network by connecting buyers, sellers, developers, and capital sources
• Oversee all operational functions of the business, including hiring, training, performance management and organizational design.
• Establish and implement policies, procedures, and internal controls to support a scalable operating environment.
• Ensure appropriate real estate, brokerage, and securities licensing and compliance across all activities.
• Partner across finance, legal, and compliance functions to ensure sound business practices, risk management, and regulatory adherence.
• Oversee key business infrastructure including CRM systems, AI tools, and technology platforms.
• Identify gaps and proactively solve problems across the business

• 12-15+ years of experience in a high-performance environment within real estate, finance, private equity, or investment-related environments.
• Strong background in deal flow, sales pipelines, and investor relationships.
• Demonstrated ability to drive revenue and close high-value transactions.
• Strong financial and investment acumen
• Highly strategic thinker with strong execution skills.
• Excellent communication skills with the ability to interface confidently with high-level stakeholders
• Highly proficient with CRM systems and AI tools
• Spanish preferred, not required
• High level of discretion, judgment, and professionalism
• Must be authorized to work in the U.S.
• Must pass a background check and provide verifiable references

Compensation: Open, commensurate on experience. Highly performance-driven compensation structure with significant upside tied to deal flow and revenue generation.