Personal Assistant

Personal Assistant

A kind, energetic and private HNW principal based in New Canaan, CT is seeking a highly organized, tech-savvy, and discreet Personal Assistant.

This is an incredible opportunity for a builder and systems-creator to establish a streamlined, digital infrastructure for a bustling, multi-property estate and lifestyle. The ideal candidate possesses a unique blend of high emotional intelligence, a warm and energetic demeanor, and sharp technical acumen.

You will work closely with a positive, fast-paced principal to digitize paper systems, manage sprawling vendor and property networks, and ultimately become a trusted gatekeeper.

Compensation, Hours, & Logistics

• Salary commensurate with experience: $120,000 – $165k range (slight flex ) + discretionary bonus.
• 3 weeks vacation + sick days
• Location: New Canaan, CT – based in the household
• Schedule: 5 days/week on-site initially to learn the estate and establish systems. Possibility for a hybrid structure down the line once operations are fully optimized.
• Hours: General schedule is 9:00 AM – 5:00 PM. However, a flexible mentality is essential; you must be responsive to after-hours or weekend emergencies. The principal is highly respectful of personal time but requires 24/7 peace of mind.

Key Responsibilities

Systems Creation & Digitization

• Estate Management Software: Lead the implementation and rollout of property management software across all domestic and international properties.
• Digital Transformation: Transition the principal’s current paper-reliant filing and operational methods into streamlined, highly efficient digital workflows.
• Financial & Organization Tracking: Set up robust digital filing systems and utilize QuickBooks to organize expenses, tracking, and bill-pay responsibilities.
• Happy to run errands, plan events, ad hoc tasks as needed!

Operations & Property Oversight

• Multi-Property Liaison: Act as a central point of contact for property managers and vendors across multiple properties and vendor management
• Schedule & Lifestyle Management: Manage personal calendars, appointments, and general travel logistics.

Candidate Profile & Qualifications

• 4 to 15+ years of experience as a Personal Assistant/House Manager supporting high-net-worth individuals.
• Technical Proficiency: Must be highly tech-savvy. Proficiency in QuickBooks and experience (or strong aptitude) with project management/estate management software or ability to implement this is required.
• Warm, friendly, positive, and energetic. A proactive "no task too small" attitude with the stamina to keep pace with a highly active principal.
• Absolute commitment to confidentiality and keeping a low profile is non-negotiable.

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