Director of Hospitality Operations

About Us Swank House is a growing boutique hospitality company based in Ashland, Oregon, operating a curated collection of vacation rentals, suites, and guest-focused lodging experiences. Our properties are design-forward, highly guest-oriented, and built around thoughtful hospitality rather than generic lodging. We are entering a new stage of growth and are looking for a true hospitality professional to help strengthen our systems, improve guest experience, optimize operations, and support future revenue opportunities. This is not an entry-level hospitality position. We are looking for someone with real hospitality management experience, strong systems ability, excellent written communication, and the professional judgment to help lead a growing operation. Position Summary The Director of Hospitality is responsible for the systems, communication, reporting, guest resolution, revenue-support, and administrative workflows that keep our hospitality business running smoothly. This person will become our in-house expert on our property management software and related systems. They will be responsible for troubleshooting, optimizing workflows, improving system accuracy, and helping create better operational structure across the company. The ideal candidate has a strong background in hospitality management, understands the relationship between guest experience and revenue, and has experience implementing or supporting new revenue streams within a lodging, hotel, vacation rental, or boutique hospitality environment. This position will start at approximately 20+ hours per week , with the opportunity to grow as the role expands. Key ResponsibilitiesGuest Experience & Communication Handle Tier 2 guest communication and escalated guest concerns. Manage sensitive guest issues, complaints, refund requests, special requests, and service recovery. Support Airbnb and direct booking inquiries that require professional judgment. Maintain a polished, guest-focused communication style across email, PMS messaging, phone/text, and booking platforms. Identify patterns in guest feedback and help improve the guest experience before issues repeat. Manage or support review responses and reputation management. PMS & Systems Management Become the in-house expert for our property management software and related hospitality systems. Troubleshoot PMS issues and coordinate solutions. Optimize our existing PMS workflows for better efficiency and accuracy. Help build standard processes for reservations, guest communication, add-ons, reporting, and operational handoffs. Maintain strong system hygiene, including reservation accuracy, guest notes, task flows, and communication templates. Update and improve Connecteam workflows in partnership with the property operations team. Create standardization so the business becomes less owner-dependent and more system-driven. Revenue Growth & Add-On Opportunities Support the development and implementation of hospitality revenue streams. Identify opportunities for guest add-ons, upsells, packages, partnerships, retail, extended stays, or experience-based revenue. Track performance of new initiatives and help refine them over time. Bring examples from prior hospitality roles where you helped implement or improve revenue-generating programs. Support pricing, guest value, and operational feasibility discussions. Operations, Reporting & Admin Prepare and review daily operational reports. Support invoice tracking, guest add-ons, refunds, and reservation-related financial details. Assist with payroll preparation and labor tracking. Support scheduling management from a systems and labor-control perspective. Help finalize and maintain employee handbook materials, SOPs, and internal workflows. Partner with ownership and the Property Operations Manager to improve communication, follow-through, and accountability. Marketing & Growth Support Support hospitality marketing efforts as the role grows. Assist with guest-facing messaging, offers, packages, email content, listing optimization, and promotional ideas. Help identify ways to better communicate the guest experience and increase direct booking opportunities. Marketing experience is not required, but it is strongly preferred. Ideal Candidate The right person for this role is professional, organized, systems-minded, and experienced in hospitality operations. You should be comfortable moving between guest communication, software troubleshooting, revenue strategy, and administrative follow-through. You are likely a strong fit if you: Have a solid hospitality management background. Have worked in hotels, boutique lodging, vacation rentals, resorts, or guest-focused property management. Are confident using property management software or hospitality technology. Can troubleshoot systems and improve workflows. Understand how guest experience impacts revenue and reviews. Have experience implementing or supporting revenue-generating hospitality programs. Understand the basics of hospitality revenue management. Understand labor control and scheduling efficiency. Communicate professionally and calmly with guests. Can write clearly and appropriately in guest-facing situations. Are comfortable working independently and taking ownership. Enjoy creating order, standards, and systems. Want to grow with a company instead of staying in a narrow task-based role. Required Qualifications Previous hospitality management experience. Experience using property management software, hotel software, vacation rental software, or similar operational platforms. Strong written communication skills. Strong organizational and follow-through skills. Ability to handle guest escalations with professionalism. Ability to manage confidential guest and employee information. Comfort working with technology, workflows, reports, and operational systems. Ability to work independently and make sound judgment calls. Preferred Qualifications Degree in Hospitality Management, Business, Tourism, Marketing, or related field. Experience with Guesty or similar PMS platforms. Experience with Airbnb, direct booking platforms, or short-term rental operations. Experience implementing hospitality revenue streams, add-ons, upsells, packages, retail, or guest experience enhancements. Understanding of hospitality revenue management. Understanding of labor control and scheduling efficiency. Marketing, branding, listing optimization, or direct booking experience. Experience creating SOPs, workflows, or internal training materials. Schedule This is a part-time position starting at approximately 20+ hours per week , with room to grow as the role develops. Some schedule flexibility may be available, but this role does require consistent availability, timely communication, and the ability to respond to operational needs during scheduled working hours. Management team members may also participate in a rotating night communications schedule. Details will be discussed during the interview process. Compensation $30-$34per hour, depending on experience. Compensation will be based on hospitality management experience, PMS/system experience, revenue management knowledge, communication skills, and the candidate's ability to take ownership of higher-level operational responsibilities. Why This Role Matters This position is central to the next stage of our company. We are looking for someone who can help us become more organized, more systemized, more profitable, and more consistent in the guest experience we provide. This is a strong opportunity for someone who has real hospitality experience and wants to help build the operational backbone of a growing boutique lodging company. To Apply Please submit your resume and a brief note explaining your hospitality management experience. In your application, please include examples of: Property management software or hospitality systems you have used. Any revenue-generating programs, add-ons, packages, upsells, or operational improvements you helped implement. Any marketing, revenue management, or labor-control experience you bring to the role.

Pay:

$28.00 - $32.00 per hour

Work Location:

Hybrid remote in Ashland, OR 97520