Chief Operating Officer- Miami, Florida

The Calendar Group•Miami, FL

2d•Onsite

About The Position

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.

Requirements

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

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