Job Description

An exceptional opportunity is available for an experienced Personal Assistant to support a dynamic, accomplished individual with a fast-paced personal and professional life. This role is ideal for someone who thrives on variety, precision, and high standards—and who takes pride in being a trusted right hand.

The individual is a retired founder of a globally successful enterprise and an active philanthropist with a deep passion for conservation, hunting, and fishing. The environment is formal yet human, with high expectations, direct communication, and moments that require both polish and resilience. This is not a predictable role—and that is exactly what makes it exciting.

The Personal Assistant will act as a gatekeeper, organizer, and problem-solver , managing a constant flow of requests ranging from complex travel logistics and event coordination to personal errands and administrative follow-through. The ideal candidate is highly organized, unflappable, detail-obsessed (in the best way), comfortable working directly with a strong personality, and can appreciate a dad joke from time to time.

WHAT MAKES THE ROLE UNIQUE

• Direct, one-on-one communication with no middle management
  
• A role that blends high-level executive support with hands-on personal assistance
  
• Trust, autonomy, and long-term for the right person
  
• A principal who values excellence, loyalty, humor, and competence

KEY RESPONSIBILITIES

This role spans personal, administrative, and logistical support, including but not limited to:

Calendar & Communication:

• Manage complex calendars, meetings, and appointments
  
• Take notes during meetings and manage follow-up correspondence
  
• Draft polished emails, letters, and thank-you notes
  
• Take dictated messages and manage communications with discretion
  

Travel, Events & Logistics:

• Coordinate private and commercial travel, including air and ground transportation
  
• Manage travel documentation, licenses, forms, and payment tracking
  
• Book events, dinners, and reservations; manage RSVPs
  
• 1-2x per year travel with the principal to meetings or engagements (e.g., NY or DC) preferred but not required
  

Administrative & Personal Support:

• Bill paying, filing, subscription management, and record keeping
  
• Track donations, deliveries, returns, and ongoing commitments
  
• Conduct research on individuals, organizations, and events
  
• Organize digital and physical files across diverse topics
  
• Assemble photo albums and distribute to guests and contacts
  
• Ability to assist with Social Media accounts
• Assist Mrs. with miscellaneous errands on occasion

Office & Errands:

• Order supplies and maintain the home office
  
• Coordinate vehicle servicing and personal errands
  
• Assist with light office reset when guests are present

• 7+ years of experience supporting a senior executive, private principal, or family office
  
• Exceptional  written and verbal communication skills , including strong penmanship
  
• Highly  organized, detail-oriented, and tech-savvy , with strong proficiency in Microsoft Office, Google Workspace, Outlook, calendar management, and Excel
  
• Able to  work independently , stay on task, and manage responsibilities with minimal oversight
  
• Self-motivated with the ability to  complete tasks efficiently and in a timely manner
  
• Comfortable managing  changing priorities and fluid schedules in a fast-paced environment
  
• Emotionally intelligent and confident working across  diverse personalities ; not easily intimidated (Principal is very friendly, values strong working relationships, and communicates directly)
  
• A true “go-getter”, "doer", and problem-solver who anticipates needs and creates solutions rather than obstacles
  
• Adaptable and unfazed by  direct communication styles
  
• Discreet, loyal, and deeply professional at all times
  
• Comfortable with, or aligned to, a lifestyle centered around  hunting, fishing, and conservation
  
• Knowledge of the Chicago area is important
  
• Experience handling or supporting  social media is a plus
  

SCHEDULE & COMPENSATION

• Schedule:   Full-Time pay with a seasonally adjusted workload  | Lighter periods average 10-20 hours per week, while busier seasons average 20-30 hours per week
• Flexibility to work additional hours is required, more likely to occur if needed on a weekend and during travel.
  
• Compensation: $100,000–$150,000 annually, commensurate with
  experience
• Medical stipend and generous time off (scheduled thoughtfully around responsibilities)

ADDITIONAL DETAILS

• Live-out position
• Hybrid remote and in-person
• Local to Lake Forest/Chicago area preferred
• Candidates must have their own reliable transportation
  
• No childcare or staff management responsibilities
  
• All candidates considered for this role will undergo a comprehensive background screening, employment and education verification, motor vehicle report, drug screening, and social media screening.
  

WHO WILL THRIVE HERE

This role is best suited for someone who loves being indispensable , enjoys working behind the scenes, and finds satisfaction in executing details flawlessly. If you are energized by high standards, variety, and trust—and you’re seeking a long-term role where excellence truly matters—this could be an outstanding fit.

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