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Director of Guest Experience

Remote, Remote

DESCRIPTION

COMPANY OVERVIEW

Portoro is a luxury short-term rental platform operating across multiple premier destination markets in the United States. We partner with high-quality homeowners to deliver professionally managed, design-forward homes that combine hospitality standards with operational discipline.

We are not a listing aggregator. We are a vertically integrated operating company. Our model blends field operations, guest experience, revenue management, and owner services into a unified platform built to protect brand reputation, drive performance, and scale responsibly.

Our homes operate at a premium tier, and so do our expectations. We target OTA ratings of 4.8 and above, maintain strict response SLAs, and operate with a bias toward accountability and measurable performance. Guest Experience is not a support function at Portoro, it is a core driver of revenue, reputation, and owner retention.

As we continue to grow, our focus is on building systems that elevate service from reactive problem solving to proactive hospitality. We are investing in leadership, structure, and cross-functional alignment to ensure that every stay reflects the quality of the homes we represent and the standards we operate by.

Portoro is built for operators who value ownership, clarity, and high standards. We believe luxury hospitality is earned through consistency, execution, and leadership at every level of the organization.

POSITION SUMMARY

The Director of Guest Experience owns and elevates the end-to-end guest journey across Portoro’s portfolio of luxury short-term rental homes.

This is a senior hospitality leadership role responsible for transforming Guest Experience into a performance-driven operating function that directly impacts:

  • OTA ratings and online reputation

  • SLA adherence and response times

  • Refund exposure and margin protection

  • Owner satisfaction and retention

  • Brand positioning across markets

This leader will move the department beyond reactive customer support into structured, proactive hospitality. You will build scalable systems, enforce operational discipline, and ensure consistent service standards across distributed and offshore teams.

Success in this role means delivering luxury-level service at scale without sacrificing operational control or financial performance. You will partner cross-functionally with Field Operations, Revenue Management, Marketing, and Owner Experience to align communication, in-home execution, and property readiness into one unified system.

This is a role for a disciplined builder who thrives in structured growth environments and drives measurable outcomes.

KEY RESPONSIBILITIES

Guest Journey Ownership & Service Model

  • Own the end-to-end guest experience across all markets

  • Establish a scalable, high-performance service model aligned with luxury hospitality standards

  • Transition the team from reactive support to proactive hospitality through preventative systems and structured workflows

  • Ensure consistency in tone, quality, and decision-making across all guest touchpoints

Operational Execution & Performance Management

  • Drive accountability for key KPIs, including OTA ratings, review sentiment, SLA adherence, resolution timelines, and refund exposure

  • Implement and enforce SOPs to prevent operational drift across markets

  • Build reporting dashboards that provide visibility into performance trends and root causes

  • Identify systemic guest experience gaps and implement scalable improvements

Team Leadership & Organizational Development

  • Lead and develop a high-performing Guest Experience organization, including frontline agents, supervisors, and offshore resources

  • Establish clear accountability structures and performance expectations

  • Build QA frameworks, training programs, and leadership development pathways

  • Strengthen workflow clarity and decision-making discipline

Issue Resolution & Risk Management

  • Create structured escalation frameworks for in-stay guest issues

  • Oversee refund and compensation strategies balancing guest satisfaction with margin protection

  • Analyze recurring complaints and lead cross-functional initiatives to eliminate root causes

Cross-Functional Alignment

  • Partner with Field Operations to ensure property readiness aligns with guest expectations

  • Collaborate with Revenue Management and Marketing to ensure listing accuracy and pre-arrival messaging reflect operational realities

  • Work with Owner Experience teams to align guest-facing decisions with long-term owner retention

Systems & Continuous Improvement

  • Optimize platforms such as Guesty, Breezeway, and related hospitality technology systems

  • Identify automation opportunities to improve efficiency and scalability

  • Enhance internal communication workflows to improve visibility and accountability

REQUIRED QUALIFICATIONS

  • 7+ years of leadership experience in hospitality operations, short-term rental management, property management, guest services, or customer experience

  • Proven success leading and scaling service or operations teams across multiple markets or distributed environments

  • Strong background in STR operations and OTA platforms including Airbnb, VRBO, and Booking.com

  • Demonstrated ability to improve measurable performance metrics such as guest satisfaction scores, SLA response times, operational efficiency, and cost control

  • Experience managing complex guest escalations and structured refund strategies

  • Proven track record in building systems, enforcing accountability, and scaling operational processes

  • Strong cross-functional collaboration experience with operations, revenue management, and property teams

  • Data-driven mindset with the ability to interpret KPIs and implement actionable improvements

  • Experience coaching managers and leading both local and remote teams

  • Excellent written and verbal communication skills with a consistent professional brand voice

PREFERRED QUALIFICATIONS

  • Experience in luxury hospitality or premium-tier short-term rental portfolios

  • Experience scaling hospitality operations in a multi-market growth environment

  • Advanced experience with Guesty, Breezeway, or comparable STR management platforms

COMPENSATION & BENEFITS

Salary Range: $80,000 – $95,000 annually

Benefits include:

  • Paid time off including PTO, sick time, and vacation days

  • Health insurance

  • Dental insurance

  • Vision insurance

  • Life insurance

Location: Remote, Anywhere in the USA

Job Type: Full-Time

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