Executive Personal Assistant- Westport at The Calendar Group – Westport, Connecticut

A busy entrepreneurial family in Westport is seeking a highly organized, tech-savvy Personal Assistant to support both business and household needs. This is a dynamic, hands-on role for someone who thrives on managing details, juggling priorities, and acting as a true extension of the family. The household includes two teenagers, two dogs, and two active business ventures, so flexibility, discretion, and strong problem-solving skills are essential.

Responsibilities

• Act as a trusted right-hand assistant for both personal and family-related tasks
• Manage household to-do lists and handle a wide range of administrative needs
• Support family logistics related to children, including school, medical, and scheduling needs
• Coordinate with builders and vendors related to home construction and maintenance
• Provide support for two business startups, including administrative and organizational tasks
• Handle sensitive tasks requiring discretion
• Oversee household organization and ongoing systems
• Assist with pet-related needs for two dogs
• Anticipate needs and keep everything running smoothly
  

Qualifications

• Exceptionally organized with strong attention to detail
• Tech-savvy and comfortable using digital tools, apps, and systems
• Trustworthy, discreet, and comfortable handling confidential information
• Able to manage multiple priorities independently
• Calm, flexible, and solution-oriented
• Comfortable working in a fast-paced, evolving environment
• Valid driver’s license and clean driving record
• Excellent verifiable references

Schedule: Full-time

Salary: $80K - $120K per year