Personal Assistant – Private Household
Greenwich, CT
This is a highly nuanced Personal Assistant role within a private household, suited for a technologically fluent, perceptive, and sophisticated professional who thrives in a fast-moving, highly personal environment.
This position requires sound judgment, discretion, situational awareness, and the ability to operate calmly and independently. Success in this role is often quiet, anticipatory, and largely invisible.
This is a modern private service role. The household values clarity, efficiency, and thoughtful use of technology — including emerging tools such as AI — to enhance organization, communication, and decision-making. The ideal candidate is intellectually curious, digitally confident, and motivated to continue learning as tools and systems evolve.
This role is not suited for entry-level assistants, candidates who require rigid structure or constant direction, or those uncomfortable working independently in a highly visible, personal setting.
A steep learning curve is expected, even for experienced assistants.
Core Responsibilities
Daily Flow, Scheduling & Communication
- Manage and maintain the principals’ daily schedules with attention to pace, transitions, and evolving priorities
- Anticipate conflicts, flag concerns proactively, and adjust plans calmly as changes arise
- Monitor and manage email and digital communications with discretion, context, and sound judgment
- Draft polished correspondence and communications that reflect the principals’ voice and preferences
- Serve as a reliable point of continuity between the principals, Chief of Staff, and household vendors
- Maintain impeccably organized digital and limited hard-copy files, including personal records, itineraries, subscriptions, and household documentation
- Use modern digital tools to track follow-ups, returns, reminders, and administrative loose ends promptly and thoroughly
Personal & Medical Support
- Coordinate medical appointments, prescriptions, and related logistics with sensitivity and confidentiality
- Maintain accurate digital records and track follow-ups as needed
- Attend appointments when appropriate to take notes and ensure continuity of care
Household Awareness & Support
- Support pet care logistics in coordination with household staff
- Serve as part of the household security contact structure
- Maintain awareness of household rhythms, preferences, and expectations
Required Profile & Professional Attributes
- Exceptionally strong organizational skills paired with mature judgment
- Ability to prioritize independently without needing constant reassurance or instruction
- Calm, steady, and composed demeanor, even amid changing plans or emotional nuance
- Discretion and professionalism when handling sensitive personal and financial information
- Strong written communication skills with a refined understanding of tone and context
- High level of comfort with technology and digital systems, including Apple devices, Microsoft Office, Google Suite and evolving productivity tools
- Intellectual curiosity and openness to using AI and automation thoughtfully to improve accuracy, efficiency, and organization
- Ability to operate effectively from a smartphone when managing real-time changes
- Observant, proactive, and able to anticipate needs rather than simply react
- Comfortable working closely with others while maintaining appropriate professional boundaries
This role is best suited for someone who has experience in a similarly nuanced environment, or who brings an unusually high level of maturity, situational awareness, and intellectual adaptability for their level.
Schedule & Flexibility
This position requires flexibility. Core hours are primarily weekday-based; however, availability outside standard hours is required at times for urgent matters, last-minute changes, or remote support. Responsibilities may evolve as household needs change.
Candidates who prefer rigid structure, constant direction, or who are uncomfortable adopting new technology may find this role is not the right fit.