Guest Services Specialist

Commitment to Excellence: Continuously raising the bar and setting new standards in guest communications and service delivery. 
Exceptional Collaboration: Thriving in a fast-paced, high-performance environment built on clear communication and teamwork. 
Unified Purpose: Aligning behind a shared mission to drive success with an intense focus. One shared consciousness. 
Data-Driven Decision-Making: Prioritizing data and results over emotions when making objective, professional decisions. 
Emphasis on Details: Details matter at every level. Leaders are expected to have a deep understanding of the specifics and adopt a hands-on management style.

Our company embraces a management style inspired by the ideals of "founder mode," as championed by Airbnb’s Brian Chesky. This means a hands-on, visionary approach to leadership, with a relentless focus on innovation, product excellence, and customer-centric decision-making. We encourage proactive problem-solving, direct involvement in key initiatives, and a collaborative, high-performance culture.

To learn more about the "founder mode" philosophy and how it shapes our operations, you can explore this link. Understanding this mindset will provide valuable context for how we operate and what we value in our team members. 

We are looking for an STR Operations & Guest Services Specialist who combines genuine tech savviness with a strong grasp of what good guest service looks like. This is not a pure guest-facing role — it sits at the intersection of systems implementation, back-office coordination, and guest communications. You will work directly with the principal and take ownership of day-to-day operations across multiple platforms.

Your Main Responsibilities:

Guest Services & Communications

• Serve as the primary point of contact for in-stay guests, handling inquiries, troubleshooting, and escalations via email, chat, and text.

• Manage OTA messaging across Airbnb, VRBO, Expedia, and Hotel Tonight — promptly and professionally.

• Monitor guest reviews across platforms; flag negative reviews for owner approval before drafting and posting responses.

• Communicate guest-reported maintenance or housekeeping issues to the appropriate personnel and log them in Turno.

• Track guest payments and manually process Expedia card charges as needed.

• Filter and triage incoming emails, routing to the appropriate party or handling directly when within scope. Tech Implementation & Systems Management

• Lead the full implementation of EnsoConnect AI messaging, including setup, configuration, and ongoing optimization.

• Handle data entry and setup for Siteminder, Airbnb, and Hotel Tonight channel management.

• Create and maintain the team's Slack and Google Workspace structure — channels, naming conventions, shared drives, and documentation organization.

• Support adoption of new tools as the tech stack evolves (including potential Trellis integration).

• Learn new platforms quickly and take ownership of how they are used operationally.

• Handle data entry for new property onboarding into Guesty and connected OTA listings.

• Maintain and update operational documents, SOPs, and internal reference materials.

• Keep OTA listings current — property details, photos, rates, and descriptions.

• Coordinate with housekeeping and maintenance vendors as needed to keep operations running smoothly. Future Responsibilities (Growth Track)

• Support marketing initiatives via Vintory, including identifying properties with below-average reviews and executing targeted email drip campaigns.

• Guesty (PMS — primary platform for reservations, listings, and reporting)

• EnsoConnect (AI guest messaging — active implementation project from day one) Also in Use:

• Turno (turnover and cleaning coordination)

• Siteminder (channel management) • Airbnb, Expedia, Hotel Tonight (OTA platforms)

• Slack and Google Workspace (team communication and documentation)

• Trellis — trellistech.com (potential addition) 

What We’re Looking For:

Excellent written and verbal English — guest-facing communication must be professional, warm, and clear.

• Prior experience in STR, vacation rental, or hospitality operations.

• Proven hands-on experience with Guesty or a comparable PMS (e.g., Hostaway, Lodgify, Track).

• Strong tech aptitude — you enjoy learning new tools, figuring out how systems connect, and building processes that scale.

• Organizational mindset: you can build a clean Slack workspace, maintain a living document library, and create repeatable workflows.

• Ability to work independently with minimal oversight in a fully remote environment.

• High attention to detail, especially around financial tasks like payment tracking and card processing.

• Calm, professional approach to guest issues — empathy and de-escalation come naturally to you.

• Critical thinking and good judgment about when to handle something vs. when to escalate. 

Nice to Haves

• Direct experience with EnsoConnect or another AI-powered guest messaging platform.

• Experience with Siteminder or other channel managers.

• Familiarity with Vintory or STR marketing/review strategy.

• Experience managing listings on Hotel Tonight or Expedia specifically.

• Background in revenue management or exposure to Pricelabs (note: pricing decisions remain with the principal).

• Internet speed minimum 30mbps: Needs to be Wired (Buy a dongle if no LAN port)
• i5 11th Gen or higher
• Windows 11 / MacOS Catalina or higher
• Minimum of 8 GB RAM
• Private and quiet dedicated home office area (no roosters, dogs, children's noises in the background)
• Back-ups in case of power or internet provider interruptions
• Good headset and webcam (preferably noise-canceling headset)

• Competitive Salary — We offer a competitive salary that reflects the candidate’s experience, skills, and responsibilities.
• Remote Work — This role is 100% remote, allowing flexibility and eliminating daily commute.
• Paid Time Off — Standard leave entitlements (vacation, sick leave, vacation leave) for rest and well-being.
• HMO Coverage — Company-provided HMO plan, offering access to medical services via accredited hospitals and clinics under a Health Maintenance Organization. This helps ensure employees have access to routine checkups, consultations, and coverage for medical care.