Personal Assistant – Roslindale, MA 

About the Role
A former semi-retired tech CEO seeking a highly capable, detail-oriented, and discreet Personal Assistant to help streamline both personal and household management. The top priorities in this role include calendar and scheduling management, administrative paperwork (particularly related to insurance and finance), contractor sourcing and negotiations, and household organization. The client can provide guidance and training for the more technical administrative tasks, but it will be an ongoing part of the job.

Key Responsibilities

1. Scheduling & Calendar Management

• Maintain and coordinate a busy calendar, prioritizing key meetings and appointments.

• Schedule professional meetings with attorneys, consultants, and other stakeholders.

• Ensure timely follow-up and preparation for all scheduled engagements.

2. Administrative & Paperwork Support

• Handle documentation and paperwork related to insurance, financial matters, and personal affairs.

• Organize and prepare materials for taxes, claims, and other administrative processes.

• Maintain up-to-date records and filing systems (digital and physical).

3. Contractor Sourcing & Oversight

• Research, vet, and coordinate with contractors and service providers.

• Assist in negotiations, contracts, and managing vendor relationships.

• Track projects and follow through on deliverables and timelines.

4. Household Organization

• Create and maintain household systems for managing supplies, bills, and records.

• Organize storage areas, manage incoming mail, and streamline home logistics.

• Coordinate maintenance services and support occasional event or guest preparation.

Additional (Lower Priority) Tasks

• Light support for managing a rental property and vacation home projects.

• Occasional help with family property logistics, as time permits.

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Ideal Candidate Attributes

• Highly Organized & Proactive: Comfortable working independently, prioritizing tasks, and creating order.

• Discreet & Trustworthy: Able to manage sensitive financial and personal information with confidentiality.

• Strong Communicator: Clear and professional written and verbal communication.

• Tech-Savvy: Comfortable with spreadsheets, cloud file systems, email tools, and basic tech troubleshooting.

• Resourceful: Skilled in researching vendors, solving problems, and adapting to changing needs.

• Financially Literate: Experience with basic budgeting, bill management, and paperwork is a plus.

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Position Details

• Location: Roslindale, Boston, MA (hybrid: combination of in-person and remote work, but mainly in person in the beginning)

• Schedule: Full-time or near full-time, with some flexibility

• Work Environment: You’ll be the sole staff member, so the ability to work independently and take initiative is essential. 
  
  $60/hour