Job Description

A private household in Winnetka is seeking a detail-oriented and experienced House Manager/Personal Assistant to take full responsibility for the smooth day-to-day operation and upkeep of the main residence and vacation home. This is a full-time, in-person position and will be based at the Winnetka property, operating primarily Monday through Friday and will require flexibility for after-hours or weekend needs. The House Manager/Personal Assistant will oversee all household logistics, maintenance, and vendor relationships to ensure the home is meticulously maintained to the highest standards. The position calls for an organized, resourceful professional who thrives on managing details, anticipating needs, and creating efficient systems. This offers a competitive salary between 125-150k depending on experience.

Key Responsibilities of the House Manager/Personal Assistant:

• Manage all aspects of daily household operations, including property maintenance, scheduling, and vendor oversight
• Develop and implement maintenance schedules, ensuring timely attention to all property needs
• Oversee household budgets, expense tracking, and inventory management
• Coordinate and supervise service providers, contractors, and seasonal projects
• Provide oversight during home renovations and special projects
• Maintain household organization systems across closets, storage, pantry, etc.
• Maintain high standards of cleanliness, organization, and presentation throughout the property
• Tech savy; knowledge with smart home systems and troubleshooting
• Handle household correspondence, documentation, and record keeping
• Provide day-to-day support to household members while maintaining discretion and professionalism
• Establish systems and procedures that enhance efficiency and consistency within the household
• Act as the primary point of contact for all external vendors, including landscapers, security, and property management

Qualifications of the House Manager/Personal Assistant:

• Minimum of 5–7 years of experience managing a private household, estate, or similar high-end property
• Strong leadership, communication, and problem-solving skills
• Excellent organizational abilities and meticulous attention to detail
• Comfortable managing budgets, expenses, and operational systems
• Tech-savvy and proficient with scheduling and household management tools
• Self-motivated, proactive, and able to anticipate needs before they arise
• Committed to maintaining the highest level of confidentiality and professionalism

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