Personal Assistant

Position: Full-Time or Part-Time Personal Assistant (Live-Out)
Schedule: Ideally MondayFriday 10:00am4:00pm with flexibility for occasional evenings or adjusted hours as needed
Compensation: Starting at $50/hour with flexibility for higher compensation based on experience
Start Date: Flexible for the right candidate
Relocation: No local candidates preferred
Perks: Free valet parking provided; mileage reimbursement at IRS rate (excluding commute); all approved work-related expenses covered

A warm optimistic and highly intelligent principal located in downtown Boston is seeking a compassionate organized and proactive Personal Assistant to help support day-to-day life scheduling and recovery-related needs. Prior to experiencing a stroke the principal practiced law for more than 25 years and continues to approach life with resilience positivity and determination.

The role is based out of a beautiful condo in one of Bostons most vibrant neighborhoods and offers the opportunity to build a meaningful long-term working relationship while genuinely improving someones quality of life and independence.

The principal is highly functional and independent in many areas including mobility personal care exercise and overnight self-sufficiency. However support is needed with organization communication scheduling technology and practical day-to-day management. The principal experiences speech aphasia and has more difficulty with reading and writing so patience excellent communication skills and emotional intelligence are especially important in this role.

Responsibilities will vary day-to-day and may include:

• Managing and maintaining calendars appointments and schedules
• Coordinating medical dental and personal appointments
• Accompanying the principal to appointments when appropriate
• Assisting with weekly medication organization and pill pack preparation
• Helping manage emails texts and phone communications including filtering spam
• Organizing contacts and information on iPhone or similar devices
• Supporting travel arrangements including booking flights coordinating airport assistance and transportation logistics
• Researching and booking cultural educational and recreational activities throughout Boston
• Assisting with password management and technology organization
• Reviewing physical mail and helping prioritize follow-up actions
• Scanning and organizing documents in PDF format for bookkeepers and other professionals
• Reviewing medical portal notes for accuracy and assisting with follow-up tasks
• Coordinating household vendors and service providers including cleaners repair professionals and technology specialists
• Running errands shopping and assisting with household logistics
• Supporting practice and use of phones tablets computers and apps
• Assisting with reading writing and conversational practice in a patient and encouraging manner
• Providing general administrative and personal support to help maintain a smooth organized daily life

The ideal candidate is organized patient adaptable and genuinely enjoys helping others live fuller more independent lives. This role is perfect for someone who is emotionally intelligent resourceful and able to balance professionalism with warmth and compassion.

Candidates should be naturally proactive detail-oriented and comfortable managing a wide variety of tasks independently. The principal is looking for someone who can become a trusted long-term support person and who values meaningful work and human connection.

Successful candidates will be:

• Calm dependable and discreet
• Tech-savvy and comfortable assisting with phones apps and digital organization
• Excellent communicators with strong listening skills
• Flexible and adaptable as needs evolve
• Comfortable working both independently and collaboratively
• Positive encouraging and emotionally mature
• Highly organized with strong follow-through

• Prior experience in a personal assistant executive assistant caregiving concierge or similar support role preferred
• Excellent references
• Legal to work in the United States
• Valid drivers license
• Comfortable occasionally driving or accompanying the principal to appointments and activities
• Strong organizational and administrative skills
• Comfortable using Apple products apps email and digital scheduling systems
• Ability to maintain confidentiality and professionalism at all times
• Experience supporting individuals recovering from medical conditions is a huge plus

• Hourly compensation starting at $50/hour with flexibility based on experience
• Weekly or bi-weekly payroll available based on employee preference
• Payment provided via direct deposit
• All approved work-related expenses reimbursed
• Free valet parking included at the building