About the Role
Open Air Homes manages premium short-term and monthly furnished rentals across Los Angeles and Palm Springs. We have grown fast, and we are hiring a Director of Homeowner Operations to own the two things that matter most to our owners: that their home is operationally dialed in, and that they trust the people running it.
This is a senior leadership role, reporting directly to the CEO and operating as a peer to our VP of Guest Experience and Hospitality. You own the homes. The buck stops with you on property operations, homeowner relationships, cost discipline, and the field team that keeps every property guest-ready.
This is not a reactive seat. We are looking for someone who anticipates problems before they reach the owner, builds the systems and standards that prevent recurring issues, and is the calm, credible voice a homeowner trusts when something needs to be handled. If you have run a portfolio of short-term or vacation rentals and owned the owner relationship, you already know exactly what this job is.
What You Will Own
Homeowner Relationships and Retention
- Serve as the senior point of contact and trusted advisor for homeowners across the portfolio
- Own owner retention: anticipate concerns, get ahead of recurring issues, and make owners feel their most valuable asset is in expert hands
- Lead homeowner conversations, including difficult ones, with credibility and a clear plan
- Present cost breakdowns, improvement recommendations, and operational plans that show owners their home is being run intelligently and cost-effectively
Property Operations
- Own operations across every home: turnovers, maintenance, vendor management, quality control, and onboarding handoffs
- Build and enforce presentation and condition standards so every property is consistently guest-ready
- Establish systems that catch and prevent recurring issues rather than reacting to them repeatedly
- Ensure operational readiness across pools and spas, HVAC, access systems, and all property systems
Cost Discipline
- Protect owner economics: get the right outcome without unnecessary spend
- Own vendor relationships and hold vendors accountable to quality, timelines, and fair pricing
- Exercise and teach sound judgment on when to dispatch, when to troubleshoot remotely, and when to escalate
Team Leadership
- Lead and develop the field operations and property management team
- Set priorities, build accountability, and run a team that anticipates rather than reacts
- Partner with the VP of Guest Experience and Hospitality to ensure seamless coordination between the guest side and the operations side
Requirements
- Direct experience managing short-term rental, vacation rental, or furnished property operations at the portfolio level. This is a hard requirement, not a preference
- Proven experience owning homeowner or client relationships, including retention and de-escalation conversations
- People leadership experience, with a track record of running a field or operations team to a consistent standard
- Strong operational judgment on vendors, maintenance, cost control, and property systems
- Excellent written and verbal communication, with the presence and credibility owners trust
- Comfort using modern tools daily, including AI tools like Claude, property management platforms, and cloud-based systems
- Reliable transportation and willingness to be in the field across greater Los Angeles
- Weekend and off-hours availability as operational needs require
Strongly Preferred
- Experience at a short-term or vacation rental management company in an owner-facing or operations leadership role
- Familiarity with the Los Angeles and Palm Springs markets
- Working knowledge of STR permitting, occupancy dynamics, and pricing
- Experience building SOPs and operational systems that scale
Benefits
- Medical, dental, and vision insurance
- 401(k) with company match
- Paid time off and paid sick leave
- Performance bonus tied to homeowner retention and operational results
- A senior leadership seat at a fast-growing company with room to shape how we operate
Pay: $110,000.00 - $130,000.00 per year
Benefits:
- 401(k)
- 401(k) matching
- Dental insurance
- Health insurance
- Life insurance
- Paid time off
- Vision insurance
Application Question(s):
- Describe your experience managing short-term or vacation rental properties at the portfolio level. How many homes, in what markets, and what was your exact role?
- Tell us about a time a homeowner or client was frustrated and considering leaving. How did you handle the conversation, and what was the outcome?
- Describe the largest field or operations team you have led, and how you held them accountable to a standard.
Work Location: In person
