PROPERTY MANAGEMENT & OPERATIONS ASSISTANT
Short-Term & Long-Term Rentals | San Diego, CA (Mission Beach)
Part-Time with Full-Time Potential | $20–$25/hr | 1099 Contractor
POSITION DETAILS
Location
San Diego, CA (Mission Beach & Hillcrest)
Schedule
Thursday–Sunday | 10–15 hours/week
Pay
$20–$25/hour | 1099 Contractor
Portfolio
6–15 Short-Term & Long-Term Rental Properties
Commitment
Minimum 1 year | Part-Time → Full-Time potential
Experience
2–5 Years in Operations, Hospitality, or Property Mgmt
ABOUT US
A little about us - we invest in real estate and currently manage our own portfolio. We have 3 kiddos ages 3, 5, 7 and a very sweet boxer. We are an active family, enjoy being outside, playing and building relationships in our community. We look forward to hearing more about you and seeing if it’s a good fit!
We’re looking for a highly organized, proactive, flexible, and friendly person to support our short-term rentals in addition to personal errands and property management activities. This role involves being in and around our home and properties regularly, so trust, communication, and good boundaries are essential. We’re hoping to find someone we genuinely click with, someone who takes initiative, solves problems independently, communicates clearly, and enjoys making systems run more smoothly for others. Even better if you have an interest in real estate and want to learn more! Must be willing to commit at least 1 year to the role. This role has potential to increase hours in the next year and even move to full time based on performance.
WEEKLY SCHEDULE
Thursday & Friday
Errands, personal tasks, and property management — 10am to 2pm (~8 hrs total, some flexibility)
Saturday
Remote work: respond to guest needs as they arise throughout the day; occasional on-site post-checkout walk-throughs (~2 hrs)
Sunday
On-site walk-throughs & inventory checks at Mission Beach and Hillcrest (12–2pm); guest responsiveness throughout the day (~4 hrs)
WHAT YOU'LL OWN
Guest Experience & Reviews
- Serve as the primary point of contact for all guest communication from inquiry through checkout
- Respond quickly and warmly to guest messages via app or text — including during weekend stays
- Proactively anticipate guest needs and resolve issues before they escalate
- Monitor, respond to, and strategically manage reviews across Airbnb, VRBO, and other platforms
- Refine messaging templates, house manuals, and check-in/check-out processes over time
Property Operations
- Oversee all aspects of property readiness — cleanliness, supplies, maintenance, and staging
- Coordinate and communicate regularly with cleaners; conduct post-checkout walk-throughs and inventory checks on-site
- Meet vendors and contractors on-site when needed; manage scheduling and follow-up
- Build and maintain a reliable vendor network for repairs, maintenance, and emergencies
- Conduct regular property inspections to ensure consistent quality standards
Listings & Platform Management
- Manage listings across Airbnb, VRBO, and any direct booking platforms
- Keep listing content (photos, descriptions, amenities, pricing) accurate and optimized
- Implement and manage dynamic pricing strategies to maximize occupancy and revenue
Errands & Personal Assistance
- Run household and property-related errands: groceries, returns, supply pick-ups, and drop-offs
- Handle small household organizing projects and ad hoc personal tasks
- Help manage calendars, schedules, and to-do lists to keep everything running smoothly
Systems & Process Ownership
- Create and maintain SOPs for all recurring operational tasks
- Identify inefficiencies and implement scalable solutions as the portfolio grows
- Leverage property management tools (Airbnb, VRBO, and PM software) to stay organized
- Provide regular operational updates to ownership
WHO YOU ARE
Experience & Qualifications
- 2–5 years of experience in operations, property management, hospitality, or a closely related field
- Demonstrated ability to manage multiple priorities, properties, and personalities simultaneously
- Experience coordinating with vendors, contractors, and/or cleaners
- Reliable transportation and proximity to Mission Beach and Hillcrest — you'll be on-site regularly
- Comfortable working in and around someone's home, with young children and a dog
The Person We're Looking For
- Integrity: You do what you say, every time.
- Accountable: You own your outcomes — when something goes wrong, you fix it and learn from it.
- Guest-Obsessed: You genuinely care about the experience guests have and take pride in earning 5-star reviews.
- Hyper-Organized: Nothing falls through the cracks on your watch. You think in systems and checklists.
- Calm Under Pressure: Maintenance emergencies, difficult guests, last-minute turnovers — you handle it with composure.
- Self-Starter: You don't need to be told what to do. You identify what needs to be done and you do it.
- Strong Communicator: Clear, professional, and timely — with guests, vendors, and our family alike.
- Trustworthy: You respect the boundaries of working in and around a family's home and honor confidentiality.
You Might Be a Great Fit If You:
- Are organized, reliable, and proactive (think Type A personality)
- Communicate clearly and check in often
- Great problem solver, like to tackle challenging tasks and find efficient resolutions
- Take initiative and solve problems before they escalate
- Ability to trouble shoot on your own with little direction
- Not afraid to take on new tasks/projects
- Can easily step outside your comfort zone
- Respect boundaries and are comfortable in someone’s home (with young kiddos and a dog)
- Enjoy making things smoother for others
- Have your own car and live nearby
- Honor confidentiality and privacy
Bonus Points
- Experience with Airbnb, VRBO, or property management software (Hostfully, Guesty, etc.)
- Background in hospitality, personal assistant, or executive assistant roles
- Genuine interest in real estate investing and the STR industry
- Active real estate license
WHY JOIN US
- Real ownership of a growing business. Your work directly shapes our reputation and day-to-day life
- Part-time flexibility now, with a genuine path to full-time as our portfolio scales
- A warm, low-ego family environment where great work is recognized and valued
- Learn the ins and outs of real estate investing and short-term rental operations firsthand
- We start with a casual meet + paid trial, no pressure, good fit on both sides or we move on
HOW TO APPLY
Send a quick intro, your resume, and responses to the questions below to:
[email protected] and [email protected]
APPLICATION QUESTIONS
Please respond to all of the following in your application email:
1. Tell us briefly about your experience with short-term rentals, hospitality, or personal assistant work. What parts of that work do you enjoy most?
2. This role requires a minimum one-year commitment and availability Thursday through Sunday, including responsiveness during guest stays. Please confirm your availability and briefly explain any scheduling considerations we should know about.
3. How do you stay organized when juggling multiple tasks, properties, or priorities at once?
4. Please describe your access to reliable transportation and your proximity to Mission Beach and Hillcrest.
5. This role involves working in and around our home and properties. How do you approach professionalism, boundaries, and confidentiality in a setting like this?
6. What are your hobbies and interests outside of work?
We look forward to hearing from you! We'll start with an interview, a casual meet, and a paid trial. If it feels like a fit on both sides, there's real opportunity here to grow into a long-term, trusted role.
Job Type: Part-time
Pay: $20.00 - $25.00 per hour
Work Location: In person
