Part-Time Personal Assistant (Highland Park / 10–15 hrs / $35–40/hr)

Overview

I am a startup founder and executive looking for a highly organized, proactive Personal Assistant to help manage the complexities of my personal life so I can remain focused on my professional responsibilities. This is a "lifestyle operations" role—you are the person who ensures nothing falls through the cracks at home or in my private affairs. While the work is primarily personal, you will occasionally interface with my professional team to coordinate calendars and ensure my personal and professional lives are in sync.

This role is best suited for someone who has supported a founder, executive, or high-net-worth household before.

Key Responsibilities

- Mail & Bill Management: Retrieve physical mail, scan/organize important documents, and ensure all personal bills (utilities, registrations, etc.) are paid on time to avoid lapses.
- Inbox Management: Monitor personal email for action items, filter spam, and draft responses for travel, services, or family-related inquiries.
- Vendor Coordination: Source, vet, and schedule third-party service providers (house cleaners, mechanic etc) and handle specialty errands (e.g., dropping my car off at a mechanic).
- Childcare: Coordinate babysitters when needed. Occasionally you may be asked to help out with childcare directly (e.g. a pick up or drop off or covering for an hour), but mostly this will be handled by a babysitter or nanny.
- Travel Logistics: Research and book personal/family travel, including flights, hotels, and dinner reservations.
- "Chief of Dad Tasks": Manage family-related logistics, such as organizing birthday parties (rentals, invites, cake) and sourcing/purchasing holiday gifts.
- Calendar Syncing: Liaise with my Executive Assistant or company staff to ensure personal appointments do not conflict with board meetings or key business milestones.

Requirements

- Discretion: You will have access to my home, mail, and private accounts. Absolute confidentiality is a non-negotiable requirement.
- Location Requirement: Candidates must reside within an ~8 mile radius of Highland Park to ensure a sustainable commute and the ability to assist with local errands and occasional on-call childcare needs.
- Proactivity: You don't wait for a reminder. If you see a bill is due or a birthday is coming up, you've already researched the solution.
- Tech Literacy: Proficiency in Google Workspace, Slack, and digital payment/scheduling apps.
- Reliable Transport: Must have a reliable vehicle for local errands.

Compensation & reimbursement

- Hourly rate: $35-40, depending on experience
- Travel reimbursement: $0.70 per mile for local errands.

IMPORTANT: please include a link to your LinkedIn profile at the top of your application. Thank you!