Stayd Collective

Stay'd was built by operators, for operators.

We believe the best local vacation rental companies deserve institutional-grade resources without sacrificing what makes them special: their brand, their people, and their community roots.

Our founding operators collectively manage more than 2,500 units across Florida, the Carolinas, and Texas. We are building a new kind of hospitality collective, one where high-performing vacation rental companies can scale with the support of enterprise-level systems, leadership, and operational infrastructure while still maintaining their individuality.

At Stay'd, companies retain their local identity and culture while gaining access to powerful shared resources, operational support, and long-term growth opportunities.

We are also deeply technology forward. We believe the future of hospitality belongs to teams that know how to combine exceptional human service with smart systems, automation, and evolving technology. We are constantly testing, improving, and adopting tools that help our teams operate more efficiently and deliver a better guest experience at scale.

We're looking for a Director of Guest Experience to help shape and elevate the hospitality experience across six companies within the Stayd collective. This is a fully remote role, based in the US.

This role will serve as the strategic and operational leader for Guest Experience across multiple brands and markets. The Director of Guest Experience will oversee guest communication strategy, service standards, team development, escalations, SOP creation, quality assurance, and operational alignment across all six companies.

A major focus of this role will also be helping modernize and evolve the Guest Experience department through technology, AI, and operational innovation. This person will help optimize AI-assisted communication tools, automations, and operational workflows while identifying opportunities to leverage technology and AI to improve efficiency, consistency, reporting, team performance, and guest communication across the collective.

This is not a corporate CX role.

This is a hands-on operational leadership position for someone who understands hospitality at a deep level, thrives in fast-moving environments, and knows how to build scalable systems without losing the human side of guest experience.

This person will work closely with company leadership teams to improve guest satisfaction, operational efficiency, communication workflows, and team accountability while still preserving the individuality and voice of each local brand.

One moment you may be reviewing KPIs and building department strategy, and the next you may be jumping into a difficult guest escalation, refining SOPs, or helping operational leaders troubleshoot workflow gaps.

The ideal candidate understands that exceptional hospitality is equal parts people, systems, accountability, communication, and consistency, and knows how to scale all five successfully across multiple brands and markets.

• Lead and oversee Guest Experience operations across 6 vacation rental brands

• Manage Guest Experience leadership teams and support frontline team development

• Create scalable hospitality standards while maintaining each company's unique brand voice

• Improve guest satisfaction, response times, resolution handling, and review performance

• Build, refine, and audit SOPs, workflows, and escalation processes

• Analyze guest communication trends, operational gaps, and recurring pain points to drive improvements

• Oversee guest communication standards across Airbnb, VRBO, Booking.com, direct bookings, and internal systems

• Help optimize AI-assisted communication tools, automations, and operational workflows

• Identify opportunities to leverage technology and AI to improve efficiency, consistency, reporting, and guest communication

• Review escalated guest situations and guide resolution strategy

• Monitor KPIs including review scores, response times, team productivity, and resolution rates

• Help unify service standards across the Stayd collective while supporting operational growth

First 90 Days

Within the first 90 days, this role will be expected to:

• Conduct a full audit of current Guest Experience operations across all 6 companies

• Evaluate workflows, staffing structures, SOPs, QA standards, escalation handling, and communication systems

• Identify operational inefficiencies, recurring guest issues, and service gaps

• Build relationships with operational leaders across all brands and markets

• Create and present a strategic Guest Experience development plan with clear priorities, measurable goals, and implementation timelines

• Recommend scalable improvements for staffing, automation, training, communication standards, and operational alignment

• Identify opportunities for improved AI adoption, operational tooling, and automation efficiencies

• Establish baseline KPIs and accountability metrics across the collective

• Begin implementing immediate operational wins while developing a longer-term Guest Experience roadmap

• 4+ years of leadership experience in hospitality, vacation rentals, or hotels operations is required

• Strong experience leading remote and/or multi-market teams

• Deep understanding of the short-term rental industry strongly preferred

• Tech-forward, highly adaptable, and excited by evolving technology and AI tools

• Experience with platforms such as Guesty, Breezeway, Slack, Airtable, HubSpot, Conduit, AI-assisted communication tools, or similar systems strongly preferred

• Someone who embraces innovation and actively looks for smarter, more efficient ways to operate

• Proven ability to build systems and processes in fast-growing environments

• Comfortable handling high-level guest escalations and operational challenges

• Strong operational mindset with a solutions-oriented approach

• Strong written communication skills with the ability to coach others on guest messaging and tone

• Ability to balance hospitality, operations, and financial realities simultaneously

• Calm under pressure and capable of making thoughtful, fast decisions

• Bilingual (English/Spanish) strongly preferred

You'd Probably Thrive Here If You

• Naturally take ownership without waiting to be asked

• Love building structure in growing companies

• Care deeply about hospitality and operational excellence

• Get excited about technology, AI tools, automation, and operational innovation

• Can zoom out strategically while still handling day-to-day fires

• Enjoy coaching teams and raising standards

• Believe systems should support hospitality, not replace it

• Don't panic when Slack gets loud

• $80,000 base salary

• On-target earnings (OTE) up to $110,000

• PTO + flexible work environment

• Fully remote position based in the US

• Opportunity to help shape and scale a growing hospitality collective

• Fast-moving, collaborative, no-corporate-fluff environment

• Leadership team made up of real operators who understand the business firsthand

• Long-term growth opportunities within a rapidly expanding platform

If you're looking for a role where you can genuinely influence the future of hospitality operations while helping exceptional local brands scale successfully, we'd love to hear from you.

You can learn more about Stay'd and what we are building at Stayd.co