Job Description

We are seeking an experienced, poised, and proactive Personal Assistant to support a CEO/Entrepreneur in Chicago, IL and & Puerto Rico (6 months/year) . This individual will work closely with the CEO’s Executive Assistant, ensuring his personal world runs as smoothly and efficiently as his professional one. This role requires strong intuition, impeccable attention to detail, a deep sense of discretion, and a polished, fashion-forward sensibility.

The ideal candidate will have a strong educational background, high emotional intelligence, and the ability to anticipate the CEO’s needs. This individual must be comfortable operating independently, making executive decisions when appropriate, and knowing when to escalate for input. A strong sense of urgency and the ability to “read the room” are essential.

Key Responsibilities:

• Serve as the CEO’s trusted gatekeeper and lifestyle manager across personal domains
• Coordinate personal appointments, including health, wellness, skincare, and spa services
• Curate and purchase fashionable, on-trend clothing and accessories; plan and style daily outfits
• Maintain and stock home environments, including groceries, wellness items, and essentials based on CEO’s preferences
• Support hosting activities, including prepping for guests on boats and at personal residences
• Manage personal travel logistics, including coordination with properties in Miami, Chicago, and Puerto Rico
• Maintain discretion and professionalism at all times, particularly around high-profile guests or partners
• Act as an intuitive thought partner, observe and recognize patterns, preferences, and emerging needs
• Be present but not intrusive. Pick up on non-verbal cues, understand context, and respond appropriately
• Collaborate seamlessly with the CEO’s Executive Assistant to ensure full-circle support
• Provide on-the-ground assistance in Puerto Rico up to 6 months per year (housing or stipend provided)

Qualifications:

• Bachelor’s degree or higher from a respected institution
• Minimum 5+ years of experience supporting a high-performing entrepreneur or executive
• High emotional intelligence, excellent judgment, and discretion
• Strong organizational skills and attention to detail
• Flexible, polished, and able to adapt quickly to changing needs
• Willingness to relocate/live in Puerto Rico for part of the year (housing support provided)
• Comfortable working occasional nights/weekends based on the CEO’s schedule

Location: Chicago, IL & Puerto Rico (6 months/year)

Compensation & Benefits:

• $150,000 – $160,000 depending on experience
• Discretionary annual bonus
• Full benefits package
• Housing or housing stipend in Puerto Rico

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