Temporary Personal/Family Assistant- Greenwich, CT

The Calendar Group; East Windsor Hill (CT); On-site; USD 55,000 - 62,000; Full time

Job summary

The Calendar Group is seeking an experienced Temporary Family Assistant to support a Greenwich, CT family during maternity leave. The role focuses on managing schedules, coordinating travel, and handling reservations for family activities, with an emphasis on discretion and reliability.

This full-time temporary position runs from October through February, with typical hours Monday through Friday, 8:00 AM to 5:00 PM.

Qualifications

• Experience managing family calendars and scheduling.
• Ability to book flights, hotels, transportation and reservations.
• Excellent organization and attention to detail.
• Responsive, proactive and resourceful.
• Ability to adapt quickly when plans change.
• Strong judgment and discretion in private households.
• Excellent communication and follow-through.
• Proficient with Outlook and standard office/calendar tech.
• Comfortable around children and dogs.
• Valid driver’s license with clean driving record; a household vehicle is available.

Responsibilities

• Manage and coordinate family calendars, appointments, and schedules.
• Arrange travel logistics: flights, hotels, ground transport, and reservations.
• Make restaurant and personal reservations, including last-minute changes.
• Coordinate vendors, tutors, service providers, and household appointments.
• Review vendor invoices and submit to bookkeeping for processing.
• Assist with children's activities, playdates, and scheduling.
• Coordinate upcoming seasonal activities and reflect in family calendar.
• Follow up with family and service providers to close items.
• Occasional school pickup or other family logistics as needed.
• Handle weekend travel/reservation requests.

Skills

Calendar management

Scheduling

Travel booking

Reservation bookings

Organizational skills

Communication

Discretion

Adaptability

Driver's license

Outlook

Tools

Outlook

Calendar software

Job description

A private family in Greenwich, Connecticut is seeking an experienced and highly resourceful Temporary Family Assistant / Personal Assistant to provide support during current employees maternity leave. The ideal candidate will be comfortable managing a dynamic schedule, coordinating travel and appointments, handling reservations, supporting children's activities, and responding to last-minute changes. The contract will be from October through February.

Responsibilities:

• Manage and coordinate family calendars, appointments, and schedules.
• Arrange and oversee travel logistics, including flights, hotels, ground transportation, and reservations.
• Make restaurant and other personal reservations, including last-minute requests and changes.
• Coordinate vendors, tutors, service providers, and household appointments.
• Review vendor invoices and submit them to the bookkeeping team for processing.
• Assist the principal with children's activities, playdates, extracurriculars, and scheduling.
• Coordinate upcoming seasonal activities and ensure schedules are accurately reflected on the family calendar.
• Follow up with family members and service providers to ensure outstanding items are completed.
• Provide occasional assistance with school pickup or other family logistics when an unexpected need arises.
• Handle occasional weekend requests related to travel or reservations.
• Maintain clear, professional communication with the principals via WhatsApp, email, and other channels.
• Anticipate needs and proactively resolve logistical issues.

Qualifications:

• Strong experience with calendar management and scheduling.
• Comfortable booking flights, hotels, transportation, restaurants, and other reservations.
• Excellent organizational skills and attention to detail.
• Highly responsive, proactive, and resourceful.
• Able to pivot quickly and confidently when plans change.
• Strong judgment and discretion when working in a private household.
• Excellent communication and follow-through.
• Proficiency with Outlook and standard office/calendar technology.
• Comfortable around children and dogs.
• Valid driver's license, clean driving record, and willingness to drive when needed; a household vehicle will be available.

Salary: $40 - $45 per hour

Schedule: Monday-Friday, approximately 8:00 AM-5:00 PM