Demo

Chief Operating Officer

The Calendar Group
Miami, FL Full Time
POSTED ON 10/28/2026
AVAILABLE BEFORE 11/26/2026

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 a sharp, highly driven Chief Operating Officer to serve as a hands-on partner across personal assets, financial infrastructure, legal matters, and special projects. This individual will work directly with the Principal as a strategic and operational partner, bringing structure, financial rigor, sound judgement, risk management, and disciplined execution to complex matters.

The COO will work closely with the Chief of Private Office, senior executives across the Principal’s operating companies, and external advisors. The position will operate as a highly hands-on individual contributor, with the opportunity to build systems & infrastructure as the family office evolves.

The ideal candidate has 5-10 years of experience and combines strong financial and legal judgement with advanced AI capabilities. They will be a resourceful problem-solver who can evaluate complex citations, identify gaps, build workflows and programs, and implement practical solutions. An MBA, JD, or similar background is strongly preferred.


Responsibilities

  • Serve as a strategic and operational partner to the Principal, increasing their leverage across financial, legal, business, property, family, and personal matters.
  • Work closely with the Chief of Private Office to establish priorities, transition responsibilities, coordinate execution, and ensure consistent follow-through.
  • Help build the infrastructure, systems, controls, reporting frameworks, and operating rhythms of an evolving private family office.
  • Initially operate as a highly hands-on individual contributor, personally driving projects from analysis and planning through execution and completion.
  • Review financial performance, forecasts, budgets, cash flow, liquidity, financing, capital allocation, and major expenditures.
  • Coordinate banking, accounting, tax-planning, insurance, estate-planning, investment, and other financial-advisory relationships.
  • Partner with attorneys and other advisors on legal, contractual, transactional, regulatory, and cross-border matters.
  • Evaluate the performance and effectiveness of external legal, financial, tax, and other professional advisors, identifying and engaging new partners when appropriate.
  • Review and negotiate contracts, proposals, fee structures, and commercial terms, escalating material risks and concerns to the Principal.
  • Support tax-planning and optimization initiatives by coordinating with tax attorneys, accountants, investment professionals, and other specialists.
  • Oversee family-office operations and establish appropriate controls, documentation, reporting, and accountability.
  • Manage or coordinate matters involving residences, vehicles, aircraft, yachts, and other significant personal assets, as applicable.
  • Lead major property and asset-related projects, acquisitions, transactions, maintenance programs, and vendor relationships.
  • Support the acquisition and development of luxury residential properties, including diligence, contract negotiations, financing, design and finish selections, and coordination with brokers, attorneys, architects, contractors, and other specialists.
  • Support the evaluation and monitoring of select private investments, although investment management will not be the primary focus of the position.
  • Coordinate financial, legal, commercial, tax, and technical due diligence with internal and external specialists.
  • Work closely with senior executives across the Principal’s operating business to coordinate priorities and execute projects affecting the Principal or family office.
  • Serve as a central point of coordination among company executives, attorneys, bankers, accountants, investment professionals, family-office staff, and other advisors.
  • Translate the Principal’s 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.
  • Build AI-enabled workflows, automations, programs, and practical solutions that improve research, reporting, visibility, efficiency, and execution.
  • Identify and mitigate financial, operational, legal, contractual, tax, security, reputational, and execution risks.
  • Lead complex and highly confidential special projects requiring sound judgment, resourcefulness, and cross-functional coordination.


Qualifications

  • 5-10 years of experience directly supporting a principal or family office.
  • Must have a legal background. Meaningful exposure to legal and tax matters, including experience coordinating attorneys, accountants, tax advisors, and other specialists.
  • Demonstrated experience working directly with a founder, principal, family, or CEO.
  • Proven responsibility for complex financial, legal, investment, tax, operational, and personal matters on behalf of a principal
  • MBA and JD 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

$200-$400K, depending on experience

Salary : $200,000 - $400,000

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