Operations Manager

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.