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Chief Operating Officer

The Calendar Group

Our client is a highly successful founder and CEO of a large, founder-owned operating company who is building a sophisticated private family office. They are seeking an experienced Chief Operating Officer to oversee and coordinate a complex portfolio of business, investment, financial, legal, property, and personal interests. This individual will work directly with the Principal as a senior strategic and operational partner, bringing structure, financial rigor, risk management, and disciplined execution to complex matters.

The COO will work closely with the Chief of Private Office, executives across the Principals operating companies and investments, and external advisors. The ideal candidate has significant experience directly supporting a principal or family, strong finance and legal exposure, and a demonstrated ability to manage investments, tax strategy, family-office operations, significant personal assets, and other complex executive matters.

Responsibilities

  • Serve as a senior strategic and operational partner to the Principal, increasing their leverage across business, investment, financial, legal, property, family, and personal matters

  • Work closely with the Chief of Private Office to establish priorities, coordinate execution, and ensure consistent follow-through

  • Maintain senior-level oversight across operating companies, private investments, family-office activities, and significant personal assets

  • Review financial performance, forecasts, budgets, cash flow, liquidity, capital allocation, financing, and major expenditures

  • Evaluate private investment opportunities, particularly within technology, AI, software, and technology-enabled businesses

  • Coordinate financial, legal, commercial, tax, and technical due diligence with internal and external specialists

  • Monitor existing investments and identify developments, risks, and opportunities requiring the Principals attention

  • Coordinate banking, investment, accounting, tax-planning, insurance, estate-planning, and financial-advisory relationships

  • Partner with attorneys and other advisors on sophisticated legal, contractual, transactional, regulatory, and cross-border matters

  • Support tax-optimization initiatives by coordinating with tax attorneys, accountants, investment professionals, and other specialists

  • Oversee family-office operations and ensure appropriate controls, reporting, documentation, and accountability

  • Manage or coordinate matters involving residences, yachts, aircraft, vehicles, and other significant personal assets

  • Oversee major property and asset-related projects, acquisitions, transactions, maintenance programs, and vendor relationships

  • Identify and mitigate financial, operational, legal, contractual, tax, security, reputational, and execution risks

  • Serve as a central point of coordination among company executives, investment professionals, attorneys, bankers, accountants, family-office staff, and other advisors

  • Translate the Principals objectives into structured plans with clear ownership, timelines, and measurable deliverables

  • Develop concise, decision-oriented reporting that identifies key issues, available options, associated risks, and recommended actions

  • Use AI, automation, and modern technology to improve research, reporting, visibility, efficiency, and execution

  • Lead complex and highly confidential special projects requiring exceptional judgment and cross-functional coordination

Qualifications

  • 10+ years of progressively responsible experience directly supporting a principal or family office.Â

  • Demonstrated experience working directly with a founder, principal, family, or CEO.Â

  • Proven responsibility for complex financial, legal, investment, tax, operational, and personal matters on behalf of a principal

  • Strong financial acumen and experience analyzing businesses, investments, liquidity, financing structures, and capital-allocation decisions

  • Meaningful exposure to legal and tax matters, including experience coordinating attorneys, accountants, tax advisors, and other specialists

  • MBA, JD, or another relevant advanced degree strongly preferred

  • Ability to independently manage complex, sensitive, and ambiguous matters

  • Strong investment-analysis skills, with particular 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

  • Intellectual confidence and the ability to challenge assumptions constructively

  • High emotional intelligence, discretion, integrity, responsiveness, and personal accountability

  • Strong proficiency with AI, automation, and modern technology

  • Willingness to remain highly accessible and responsive as matters require

Location

Miami, Florida

Compensation

Highly competitive compensation commensurate with experience. 

Vacancy posted 3 days ago
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