The Calendar Group
The Calendar Group is a full-service staffing firm which provides professional and personalized staffing to high net worth families,
- Open roles
- 104
- New role every
- ~1.1 days
- Posting trend
- 3.2× vs prior 90d
Company signals
Score: 77Job facts
- Location
- Hybrid · Westport, Connecticut, United States of America
- Workplace
- Hybrid
- Type
- Full-time
- Posted
- Aug 21, 2026
Last verified live 1 month, 1 week ago · checked directly on the company's JazzHR / ApplyToJob
More roles at The Calendar Group
- Butler- Atherton, CA · Atherton, CA
- Housekeeper- Houston, Texas · Houston, TX
- Housekeeper- Houston, Texas · Houston, TX
- Family Assistant- Ridgefield, CT · Ridgefield, CT
- Live-in Housekeeper- UES, NYC · New York, NY
- Family Assistant- Ridgefield, CT · Ridgefield, CT
Finance Director- Westport, CT
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