Description
COMPANY OVERVIEW:
Stay Classy Homes is a leading vacation rental management company based in San Diego that specializes in providing high-quality, memorable guest experiences and exceptional service to homeowners. We operate a growing portfolio of premium short-term rentals in 4 states, and we pride ourselves on our attention to detail, personalized service, and commitment to operational excellence.
As we scale, we’re seeking a strategic and hands-on Operations Manager to lead our operational teams and processes, ensuring we deliver consistently excellent service to guests and property owners.
POSITION SUMMARY:
The Director of Operations will oversee and optimize all day-to-day field and back-office operations related to our vacation rental properties. This role requires a proactive, systems-oriented leader who can scale operations, manage distributed teams, and implement efficient processes to ensure quality, compliance, and profitability.
The ideal candidate is results-driven, thrives in a fast-paced, ever-evolving environment, and brings a confident, solutions-focused approach to leadership. They are energized by challenges, fluent in juggling competing priorities, and skilled at motivating others toward a common goal. This is a high-impact, high-ownership role for someone who leads with initiative, embraces innovation, and isn’t afraid to take bold action to move the business forward.
RESPONSIBILITIES:
1. Operations Leadership
- Oversee daily operations across all properties, including housekeeping, maintenance, property readiness, vendor coordination, and inventory management.
- Manage and optimize scheduling, inspections, turnovers, and response workflows to ensure 5-star guest experiences.
- Implement and track KPIs across key operational domains (turnover times, quality assurance, response rates, cost control, etc.).
2. Team & Vendor Management
- Lead and scale a team of local field staff, client success coordinators, and virtual assistants.
- Hire, train, and develop team members with a focus on accountability and service excellence.
- Establish strong vendor relationships and negotiate favorable contracts for cleaning, maintenance, and supplies.
3. Technology & Systems
- Leverage our property management software (Guesty), cleaning/maintenance software (Breezeway), communication tools, and internal dashboards to streamline operations.
- Identify and implement tech solutions that enhance operational efficiency and visibility.
- Oversee and implement our revenue management strategy (nightly pricing) across our portfolio
- Maintain accurate data across platforms (booking portals, pricing engines, inventory systems).
4. Owner & Guest Satisfaction
- Collaborate with guest experience and account management teams to ensure seamless service delivery.
- Resolve escalated guest issues and ensure proactive communication with homeowners.
- Support onboarding of new properties and ensure operational readiness.
5. Financial & Strategic Oversight
- Develop and manage budgets for operational functions; track against targets.
- Identify cost-saving opportunities without compromising quality.
- Contribute to strategic planning and geographic expansion by evaluating operational feasibility.
6. Compliance & Risk Management
- Ensure adherence to local, state, and federal laws regarding vacation rental regulations, licensing, and safety protocols
- Oversee insurance, vendor contracts, and incident response protocols
QUALIFICATIONS:
Minimum Qualifications - Required:
- 2+ years of operations leadership experience within short-term rental management, vacation rentals, hotel management, or residential property services.
- Experience managing remote and hybrid teams, including hiring, training, scheduling, and performance management of housekeepers, maintenance techs, and field coordinators.
- Strong vendor management skills, including contract negotiation, SLA enforcement, and sourcing local service providers for cleaning, linen, pest control, pool/spa service, landscaping, etc.
- Excellent process development and systems thinking – ability to map workflows, identify inefficiencies, and implement scalable SOPs and automations.
- Exceptional organizational and communication skills, including the ability to document processes, set clear expectations, and lead under pressure.
- Comfortable in fast-paced, dynamic environments – ideally experience in a startup or high-growth service business where adaptability and resourcefulness are essential.
Preferred Qualifications:
- 4+ years of operations leadership experience in Vacation Rental management, Hotel Management, or Property management.
- Proven track record of overseeing 100+ properties, including managing turnovers, housekeeping, maintenance, and guest service standards across multiple geographic locations.
- Direct experience implementing and managing our property management systems (Guesty) such as Guesty, Hostaway, Hospitable, or comparable platforms. Experience with short-term rental operational workflows and tech stacks (e.g. Breezeway, Monday, Pricelabs).
- Operational budgeting experience, with a strong understanding of cost tracking, gross margin improvement, and managing property-level P&Ls.
- Familiarity with local STR regulations, permitting processes, and compliance in San Diego.
- Strong knowledge of vacation rental platforms (Airbnb, VRBO) and PMS systems (Guesty, Breezeway)
COMPENSATION & BENEFITS:
Compensation:
- Annual Salary: $60,000 based on experience
- Bonus Compensation: Yes, based on meeting Operational KPI’s
Benefits:
- Paid time off, such as PTO, sick days, and vacation days
- Health insurance
- Life insurance
- Dental insurance
- Vision insurance
- Retirement benefits or accounts
Schedule
Ideally, Wednesday through Sunday from 9 AM to 5 PM, as weekends are our busiest days.