Personal Assistant

Private Principal in Boston, Massachusetts Seeking a Personal Assistant

Position: Full-Time or Part-Time Personal Assistant (Live-Out)
Schedule: Ideally Monday–Friday, 10:00am–4:00pm 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

About the Principal

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 Boston’s most vibrant neighborhoods and offers the opportunity to build a meaningful long-term working relationship while genuinely improving someone’s 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

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

Ideal Candidate & Personality

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

Requirements

• 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 driver’s 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

Compensation & Payroll

• 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