Head of Guest Experience

About Cloud9

Cloud9 is an AI-driven luxury short-term rental company transforming long-term luxury properties into exceptional short stays with hotel-quality service. Operating over 60 units in 13 Class-A buildings across Chicago, the company is expanding to multiple U.S. cities. Cloud9 integrates AI deeply into daily operations, emphasizing speed, efficiency, and outcome-focused work within a distributed team.

Role Overview

Currently, guest experience leadership rests partially with the CEO alongside many other responsibilities. The company seeks a leader to fully own and build the guest experience function from the ground up—defining standards, service level agreements (SLAs), escalation processes, quality assurance (QA) metrics, coaching routines, and eventually growing a dedicated team. This role demands establishing data-driven systems leveraging AI for guest communication, triage, alerts, and tracking performance to maintain luxury service quality.

Key Responsibilities

• Create and codify the highest standards for five-star guest response and service at Cloud9.
• Establish and monitor metrics such as median first response time under 5 minutes and 100% callback rate for missed calls within 15 minutes.
• Design comprehensive SLAs, escalation trees, and QA scorecards from scratch to be used and maintained daily by the team.
• Recruit, coach, and manage the guest experience team maintaining high performance standards and accountability.
• Control financial impact by safeguarding against excessive refunds and compensations while balancing service speed and quality.
• Develop and own the AI technology stack—large language models (LLMs), knowledge bases, automated replies, and alerting—to enhance guest service efficiency.

Success Milestones

• Within 30 days: Implement instrumentation to quantifiably measure existing guest service challenges including response times and refund levels.
• By 90 days: Define and begin tracking SLAs thoroughly; eliminate nearly all escalations to the CEO and ensure 100% callback completion.
• By 180 days: Launch a QA scorecard and weekly coaching sessions; make the first hire meeting your standards.
• By 12 months: Establish a fully staffed team with consistent SLA adherence, maintained review-score benchmarks, and controlled refund expenditures, removing CEO involvement from guest tickets.

Required Qualifications

• Proven hands-on experience designing and implementing a guest operations or customer service system from the ground up including SLAs, escalations, and QA processes, supported by quantifiable impact.
• Experience defining key metrics, establishing tracking/dashboards, and running operations based on data-driven insights.
• Proficiency integrating AI tools such as LLMs for automating knowledge bases and guest communication workflows beyond simple use of common chatbots.
• Demonstrated leadership managing teams: hiring, coaching, and enforcing performance standards strictly and fairly.
• Strong ability to create standard operating procedures independently in ambiguous, fast-changing environments.
• Confidence to challenge senior leadership constructively with evidence-based reasoning.
• Fluent English communication skills, both written and verbal.

Who Is This Role Not For

• Those experienced only with operating existing corporate hospitality systems without foundational build experience.
• Leaders who rely on intuition or team credit rather than personal direct ownership and metric-driven success.
• Individuals unprepared to fully embrace and integrate AI in their daily workflow.
• Candidates dependent on existing SOPs rather than creating them in uncertain contexts.
• Those unwilling to engage deeply in frontline guest experiences.

Additional Information

• Cloud9 fosters a high-performance meritocratic culture focused on execution, radical feedback, and top-tier talent retention.
• The team is distributed with primary operations in Chicago and Latin America.
• The hiring process includes a paid case study to assess candidate capabilities before final interviews.
• Cloud9 is an equal opportunity employer, committed to non-discrimination based on legally protected characteristics.

Why Join Cloud9?

If you desire autonomy over impactful metrics, rapid execution, and to build with AI innovation at the core, this role offers a unique opportunity to lead and scale guest experience in a fast-growing luxury rental platform. Comfort-focused roles valuing effort over outcome are not aligned with this position.