Executive Personal Assistant

We’re looking for a highly organized, discreet, and resourceful Personal & Executive Assistant to support a busy insurance agency owner. This is a hybrid role that blends business operations support, personal/household management, and family/kids coordination — ideal for someone who thrives on variety and can shift smoothly between a client email and a school pickup schedule in the same hour

• Paid Time Off (PTO)
• Health Insurance
• Retirement Plan

Business & Insurance Agency Support

• Manage the owner’s calendar, client meetings, and appointment scheduling
• Draft, proofread, and send client correspondence (emails, renewal reminders, follow-ups)
• Assist with policy documentation, filing, and CRM/data entry
• Coordinate with the agency’s direct staff and outsourced/remote team members on task follow-through
• Track deadlines for renewals, licensing, and compliance paperwork
• Prepare materials for client meetings and internal reviews
• Handle incoming calls/emails and delegate by priority

Personal & Household Management

• Manage personal calendar, appointments, and errands
• Handle bill pay, budgeting reminders, and basic bookkeeping support
• Coordinate travel planning and bookings (personal and business)
• Manage the Airbnb rental property: guest communication, cleaning/turnover scheduling, and coordination through Guesty
• Vendor and household staff coordination (cleaners, contractors, repairs)
• Personal shopping, gift purchasing, and returns
• Manage subscriptions, renewals, and household admin

Kids & Family Coordination

• Manage kids’ schedules: school, activities, appointments, and playdates
• Coordinate carpools, pickups/drop-offs, and camp or activity registrations
• Track school communications, forms, and deadlines
• Schedule pediatrician, dentist, and other family appointments
• Assist with birthday parties, holidays, and family event planning
• Pack lists and logistics for family trips

Qualifications

• 2+ years of experience as a personal assistant, executive assistant, or similar role
• Excellent written and verbal communication skills
• Strong organizational skills and ability to manage competing priorities
• Comfortable with CRM software, Google Workspace/Microsoft Office, and scheduling tools
• Experience with Guesty or other property management platforms a plus
• Discretion with sensitive family and business information
• Valid driver’s license and reliable transportation (if in-person errands/pickups required)
• Flexible, proactive, and calm under pressure
• Anticipates needs before being asked
• Equally comfortable emailing a client and packing a school lunch
• Trustworthy with confidential financial and family information
• Tech-savvy and quick to learn new tools/systems