Personal Assistant

Landmark Healthcare Facilities LLC, a well-established commercial real estate corporation based in the heart of downtown Milwaukee is seeking a tech-savvy, detail-oriented professional to serve as Personal Assistant to the Executive Chairman. This role is ideal for a self-starter who thrives in a dynamic, fast-paced environment and enjoys providing comprehensive, hands-on support across business, household, and personal domains. The ideal candidate has prior experience supporting an ultra–high-net-worth individual and understands the discretion, responsiveness, and professionalism such a role requires.

Responsibilities

• Manage and prioritize the Executive Chairman’s calendar, including professional, personal, and family commitments.
• Coordinate and confirm complex travel itineraries, including flights, hotels, ground transportation, and dining arrangements.
• Schedule and track personal appointments and affairs (local and out-of-state).
• Research and compile background information, reviews, and reports related to travel, entertainment, and other personal interests.
• Type, edit, and format business proposals, correspondence, and marketing materials as dictated by the Executive Chairman (not responsible for independently drafting content).
• Create PowerPoint decks, spreadsheets, and other high-level business documents.
• Act as gatekeeper for all calls, mail, and electronic correspondence.
• Maintain strict confidentiality and discretion at all times.
• Be available outside of standard business hours when required.

Qualifications

• Strong follow-through and problem-solving skills with exceptional attention to detail.
• Highly collaborative and thrives as the “right hand” to an executive.
• Advanced technical proficiency in Microsoft Office Suite, AI productivity tools, and Canva.
• Excellent communication and organizational skills.
• 3 years of administrative or personal assistant experience supporting a senior executive; real estate experience is a plus.
• Bachelor’s degree preferred; minimum of two years of advanced education required.
• Proven ability to manage competing priorities and maintain professionalism under pressure.
• Willingness to work in-office Monday through Friday, with flexibility for occasional evening or weekend needs.

Compensation and Benefits

Base salary starts at $70,000 annually, depending on experience, plus a year-end discretionary bonus.

Comprehensive benefits package including:

• Medical, dental, and vision insurance
• Life, short-term, and long-term disability insurance
• Health Savings Account and Flexible Spending Plan
• 401(k) with employer match
• Three weeks paid vacation and eight paid holidays
• Paid downtown Milwaukee parking