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The Calendar GroupPosted 1 week ago

Chief Operating Officer- Miami, Florida

On-siteMiami, Florida, United States

Full TimeSenior LevelStartupServices

Job Summary

Oversee and coordinate a complex portfolio of business, investment, financial, property, and personal interests while maintaining senior-level oversight across operating companies and private investments. Review financial performance, forecasts, budgets, cash flow, capital allocation, and major expenditures; evaluate private investment opportunities within technology, AI, and software sectors. Coordinate financial, legal, commercial, and technical due diligence; monitor existing investments and identify developments, risks, and opportunities. Lead complex financial, legal, transactional, and property-related matters, identify and mitigate risks, and 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 use AI and automation to improve efficiency.

Required 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

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