Chief Operating Officer- Miami, Florida in Miami, Florida at The Calendar Group

Our client is searching for an experienced Chief Operating Officer to oversee and coordinate a complex portfolio of business, investment, financial, property, and personal interests. The COO will bring structure, financial insight, risk management, and disciplined execution to the organization while collaborating with company executives, investment professionals, and external advisors. The ideal candidate is a highly capable generalist with strong financial, analytical, operational, and interpersonal skills.

Responsibilities

• Maintain senior-level oversight across operating companies and private investments
• Review financial performance, forecasts, budgets, cash flow, capital allocation, and major expenditures
• Work with CEOs, CFOs, investment professionals, bankers, accountants, attorneys, and other advisors
• Evaluate private investment opportunities, particularly within technology, AI, software, and technology-enabled businesses
• Coordinate financial, legal, commercial, and technical due diligence
• Monitor existing investments and identify developments, risks, and opportunities requiring attention
• Maintain visibility into liquidity, financing, investments, properties, and other significant financial commitments
• Coordinate banking, tax, accounting, insurance, investment, and financial-advisory relationships
• Lead complex financial, legal, transactional, and property-related matters
• Identify and mitigate financial, operational, legal, contractual, security, and execution risks
• Oversee major property projects and transactions
• Serve as a central point of coordination across internal teams and external advisors
• Develop concise, decision-oriented reporting and recommendations
• Use AI, automation, and modern technology to improve efficiency, visibility, and execution
• Lead complex special projects with discretion and sound judgment

Qualifications

• 10+ years of experience in operating, investment, financial, family office, or principal-facing environments
• Strong financial acumen and experience analyzing businesses and investments
• Experience working with senior executives, investors, attorneys, bankers, accountants, and other professional advisors
• Ability to independently manage complex and ambiguous matters
• Strong investment-analysis skills, with an interest in technology and AI
• Experience coordinating sophisticated legal, financial, tax, and transactional matters
• Excellent risk-management, organizational, and execution capabilities
• Ability to synthesize complex information into clear, actionable recommendations
• High emotional intelligence, discretion, integrity, and personal accountability
• Intellectual confidence and the ability to challenge assumptions constructively
• Strong proficiency with AI, automation, and modern technology

Location

Miami, Florida

Compensation

Highly competitive compensation commensurate with experience.