Hiring: Chief Operating Officer Company: The Calendar Group Location: Miami, FL Job Posted Time: 2026-09-16 10:20:03 About the job Experience: •10+ years of progressively responsible experience directly supporting a principal or family office. Required Skills: •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 Principal’s attention •Coordinate banking, investment, accounting, tax-planning, insurance, estate-planning, and financial-advisory relationships Qualifications: •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 •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 •Demonstrated capacity to independently manage complex, sensitive, and ambiguous matters •Strong investment-analysis skills, with particular interest in technology and AI •Excellent risk-management, organizational, and execution capabilities •Demonstrated capacity to synthesize complex information into clear, actionable recommendations •Intellectual confidence and the ability to challenge assumptions constructively Interested candidates, please apply directly through the job posting on company's career page or try via AI auto apply on this platform. Don't miss this opportunity to join a forward-thinking team!