Managing Director- Westport, CT in Westport, Connecticut at The Calendar Group

Our client, a private equity CEO based in Fairfield County, CT, is seeking a highly capable and financially minded Managing Director to oversee and optimize his personal financial ecosystem. This individual will operate as a trusted right hand, managing liquidity, financial infrastructure, household financial operations, and day-to-day financial administration with a focus on clarity, efficiency, and execution.

This role is best suited for someone who thrives in a lean, entrepreneurial environment and can seamlessly move between high-level financial strategy and hands-on execution. The ideal candidate is polished, proactive, self-directed, tech-savvy, and highly discreet. This is a unique opportunity offering significant long-term upside and the ability to grow alongside the principal as his personal office and infrastructure continue to evolve.

Key Responsibilities

• Maintain a real-time view of all assets, including public markets, private investments, real estate, and cash
• Oversee liquidity planning, including capital calls, distributions, and cash deployment
• Manage banking relationships, account structures, and cash flow across entities
• Execute wires, oversee bill pay, and ensure operational accuracy and efficiency
• Serve as the central point of contact for tax, legal, and financial advisors
• Prepare concise financial summaries, reporting, and ad hoc analyses
• Oversee financial operations across multiple properties, including transactions and vendor management
• Manage household financial operations, including payroll, budgets, and service providers
• Build and improve systems to enhance financial visibility, organization, and efficiency

Qualifications

• 7+ years of relevant experience
• Bachelor’s degree in Finance or Accounting preferred
• Background in family office, private wealth, personal CFO, Chief of Staff, private banking, or similar environments
• Experience directly supporting UHNW individuals, founders, or executives highly preferred
• Strong understanding of liquidity management and financial structures
• Experience with real estate and/or household operations preferred
• Highly organized, detail-oriented, proactive, and solutions-oriented
• Tech-forward mindset with comfort leveraging AI and technology tools to improve efficiency
• Strong judgment, discretion, and communication skills

Schedule: Hybrid; periodic in-person availability required

Compensation: Approximately $250,000 total compensation, dependent on experience