COO, AI-Driven Tech & Investment Operations

thecalendargroup; Miami (FL); On-site; USD 250,000 - 450,000; Full time

Job summary

The Calendar Group seeks an experienced Chief Operating Officer to steer a diverse portfolio of business, investment, financial, property, and personal interests from its Miami base.

You will provide financial insight, risk management, and disciplined execution while partnering with executives, investment professionals, and external advisors. A strong generalist with a tech-forward mindset is essential.

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.

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.

Skills

Financial analysis

Risk management

Operational leadership

Executive communication

Investments

Due diligence

Technology & AI familiarity

Strategic planning

Cross-functional collaboration

Decision making under ambiguity

Job description

The Calendar Group seeks an experienced Chief Operating Officer to steer a diverse portfolio of business, investment, financial, property, and personal interests from its Miami base.

You will provide financial insight, risk management, and disciplined execution while partnering with executives, investment professionals, and external advisors. A strong generalist with a tech-forward mindset is essential.