Executive Assistant

Job Title: Executive Assistant and Property Manager (San Diego, Hybrid)

CompensationPay: $1,200–$1,800/month DOE
Commitment: 10–15 hours/week (~40–60 hours/month) across at least 2-3 days per week, ideally including one weekday and one weekend day. Additional hours or tasks may be negotiated as needed.
Contract Period: 90-day probationary period followed by a 6-month contract (optional renewal).

About the Role
Serve as a trusted right hand to an active and busy executive couple to protect their limited free time, maintain the cadence of the household, and take on new challenges that serve your professional growth. This hybrid role combines executive/personal assistance with property and Airbnb management. It is ideal for a highly organized, proactive, reliable, and tech-savvy individual seeking a flexible, growth-oriented opportunity. The schedule is designed to be hybrid and flexible during weekdays, with occasional weekends and evenings required. Other business and property tasks are additionally available for those with relevant skills or a desire to be trained to take on those projects. This role offers a chance to be part of a larger mission for holistic health and wellbeing, with close mentorship and door-opening skills.

Who We are Looking For
The ideal candidate will possess strong administrative skills, exceptional attention to detail, and the ability to manage multiple tasks efficiently. This role requires a professional demeanor, excellent communication skills, and the ability to maintain confidentiality while managing sensitive information. We'd like to cultivate your unique skills and desire to grow in this role, as your capacity and interest is demonstrated after a successful 90-day training period. Candidates must be dog-friendly and live within a reasonable commute to Hillcrest/downtown San Diego.

Core Responsibilities (Must-Haves)

Household & Property Management:

• Weekly property maintenance checks, tidying, and maintenance coordination
• Managing tenant correspondence and communications
• Scheduling regular cleanings and maintenance
• Maintaining an up-to-date inventory of house supplies and materials
• Light housekeeping, home organization, and gardening
• Managing mail, deliveries, and returns
• HOA payments and utility management
• Coordinating repairs, maintenance, and troubleshooting
• Landscaping or handywork experience (bonus skill)

Administrative Tasks:

• Weekly meetings with homeowners
• Monthly expense tracking and bookkeeping data entry
• Scheduling, inbox management, and correspondence (emails, calls, appointments)
• Intensive Google Calendar maintenance and appointment scheduling (fitness, medical, legal/banking, etc.)
• Completing, filing, organizing, and archiving documents
• Bill payment and expense tracking
• Preparing documents through proofreading, transcription, and clerical duties
• Supporting project coordination by tracking deadlines and deliverables
• Maintaining professional communication while interacting with stakeholders
• Utilizing Microsoft Office Suite, Google Workspace, Dropbox, Zoom, ClickUp and other softwares for various administrative tasks

Executive Support:

• Serve as an alternative point of contact for the executive and safeguard their time
• Travel planning and booking support
• Running errands and occasional driving/accompanying the executive to appointments and meetings
• Preparing for meetings, including creating agendas and taking minutes
• Conducting research on various topics as requested by the executive
• Coordinating and managing special projects as assigned
• Handling correspondence with professionalism while managing multiple inboxes and phone lines

Airbnb Management:

• Listing updates
• Guest communications
• Check-in/out and cleaning coordination
• Rental property preparation and turnover
• Inventory and supply stocking and management

Community & Event Management:

• Support with events, gatherings, and guest logistics
• Sending holiday cards, buying gifts, and tracking important dates
• Facilitating social arrangements and group gatherings
• Coordinating and planning events, ensuring all logistics are handled effectively

Bonus Skills (Nice-to-Haves, Not Required):

• Experience with payroll, QuickBooks Online, and bookkeeping support (transaction entry, document gathering, monthly reconciliations)
• Content uploads/basic marketing support (social media, newsletters, website updates)
• Experience with ClickUp, Kajabi, Evernote, and other software
• Experience in event planning and project coordination

Ideal For:

• Recent grads, remote workers with flexible hours, “slash” creative/admin types, or career-changers
• Clean, reliable, communicative, discreet, and professional individuals
• Passionate about holistic health and wellbeing

Qualifications:

• Preferred: 3+ years of experience in an administrative, property management, or executive assistant role
• Strong technical skills: Proficiency in Google Suite, Dropbox, Zoom, and a willingness to learn new tools
• Highly organized, detail-oriented, and proactive
• Excellent communication and customer service skills
• Reliable, punctual, professional, and able to maintain confidentiality
• Self-sufficient and proactive in managing in-person, remote, and off-limit hours
• Discreet, dependable, and capable of working independently
• Must be comfortable tracking time within ClickUp and communicating promptly
• Must have a valid driver’s license, car insurance, and a reliable vehicle
• Must have a reliable internet connection
• Bachelor’s degree preferred (or equivalent experience)

Benefits:

• Flexible hybrid schedule
• Paid professional development
• Free unlimited sauna membership
• $100/mo wellness stipend after 30 days
• Parking onsite
• Comped meals while on business travel for 3+ hours
• Comped gas/mileage for personal vehicle use

To Apply:
Send your resume and a brief cover letter describing your relevant experience and why you’re interested in this hybrid support role. Please highlight any special or bonus skills you bring!

Expected interview steps:

• Applications will remain open for ~4 weeks until 11/07/25, then on a rolling basis as needed
• If your resume is selected, our Ops Manager will schedule an initial ~15 min Zoom screening, then make a recommendation for a second interview
• You will have a second round 20-30 min Zoom interview with either one or both of the business owners
• Paid final interview onsite at property to meet owners + dog and to complete a sample project task
• Job offer
• Two weeks paid training

Job Types: Part-time, Contract

Pay: $1,200.00 - $1,800.00 per month

Expected hours: 10 – 15 per week

Benefits:

• Flexible schedule
• Professional development assistance

Work Location: Hybrid remote in San Diego, CA 92103