Head of Customer Success

Location: Remote United States or Bogotá HQ
Employment Type: Full-time
Department: Customer Success
Compensation: Competitive salary + 2026 equity + performance bonus tied directly to repeat bookings, CSAT, and NPS

Overview / Application

Cloud9 exists to redefine luxury short-term rentals: uncompromising five-star standards, powered by ruthless efficiency and automation.

We don’t hire to fill seats. We hire to pull levers that move KPIs. We don’t care about intentions. We care about outcomes.

Our core values: speed, meritocracy, accountability, execution. Performance is impossible to hide.

Role Summary

This is a high-leverage growth role. If you work, Cloud9 unlocks a repeat-guest engine that compounds revenue, drives referrals, and builds a five-star brand moat.

You own the guest relationship from booking through departure and beyond. Managers who just “oversee” support will not survive here. We want doers who solve problems in minutes, not hours. Guest loyalty, referral revenue, and public review scores live or die with you.

Responsibilities (Outcomes, Not Tasks)

• Raise NPS: Drive NPS ≥70 within 6 months.
  

• Boost CSAT: Achieve and hold guest CSAT ≥4.95.
  

• Accelerate resolution: Ensure 90%+ of guest issues are resolved in <15 minutes.
  

• Grow loyalty: Increase repeat bookings by 20% YoY.
  

• Expand referrals: Deliver ≥15% of new bookings from referrals by year-end.
  

• Dominate reviews: Hold Airbnb/Booking/Google review scores at ≥4.9 across portfolio.
  

• Predict issues: Implement proactive guest communication → reduce escalations by 25%.
  

• Systemize delight: Build guest playbooks (VIP touchpoints, pre-arrival, post-stay).
  

• Data-driven CX: Launch guest insights dashboard with 90% adoption across teams.
  

• Scale team: Train “Guest Success Academy” for CS associates → 30-day ramp to full productivity.
  

Results (Success Looks Like…)

• NPS consistently ≥70.
  

• Guest CSAT holds ≥4.95.
  

• ≥20% YoY repeat bookings.
  

• 90%+ of issues resolved within 15 minutes.
  

• ≥15% of new bookings sourced from referrals.
  

• Portfolio review scores ≥4.9 across platforms.
  

• Escalations reduced by 25%.
  

• Guest playbooks validated across markets.
  

Requirements

• 5+ years in guest/customer success (luxury hospitality, boutique, or tech-enabled STR).
  

• Proven record of driving NPS, CSAT, or repeat bookings.
  

• Tactical execution skills: show KPIs moved and how.
  

• Player-coach leadership style — leads while executing.
  

• Master communicator: written, verbal, escalation handling.
  

• Bonus levers: Referral systems, review management, loyalty program design.
  

⚠️ Interview warning: You will be asked to walk step-by-step through how you moved a KPI in your last role. If you can’t, you don’t pass.

Who This Role is NOT For

• People who confuse effort with results.
  

• Managers who only oversee support tickets.
  

• Anyone afraid of direct, real-time feedback.
  

• Those who protect feelings over standards.
  

Compensation, Benefits & Relocation

• Competitive salary + 2026 equity + performance bonus tied directly to repeat bookings, CSAT, and NPS.
  

• PTO (accountable use).
  

• Relocation support to Bogotá HQ if desired.
  

Core Values

• Meritocracy – Outcomes > effort. Performance is public.
  

• Execution – Doers win. Prioritize, test, deliver fast.
  

• Radical Feedback – Real-time corrections. No politics.
  

• Championship Team – Only A-players. Mediocrity cut fast.
  

7/30/90 Day Scorecard

• Day 7: Deliver baseline CSAT/NPS dashboard.
  

• Day 30: Launch guest resolution playbook pilot.
  

• Day 90: NPS ≥70, CSAT ≥4.95, 90%+ resolution in <15 minutes. Repeat bookings + referrals trending up.
  

Cloud9 is not a family. It’s a championship team. If you want to build the guest loyalty engine of scalable luxury hospitality, apply now.