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Director, Owner Experience

United States, Remote

About Pacaso:
Pacaso exists to enrich lives by making second home ownership possible and enjoyable for more people. Our innovative co-ownership model is the easiest, smartest and most responsible way for people to experience the joy of a second home. We provide all the benefits of true ownership without the hassles through our simplified financial structure, easy and equitable scheduling, and dedicated local property management.Founded by former Zillow executives, Pacaso has facilitated over $1 billion in gross real estate transactions and service fees across more than 40 markets nationwide, as well as internationally in Paris, London, and Cabo.

We have been featured in The New York Times, Wall Street Journal, Fortune, Forbes, CNBC and more.Pacaso is a certified Great Place to Work and has received numerous accolades for its workplace culture. Fortune and Great Place To Work named Pacaso to the 2024 Best Workplaces in Real Estate list. In 2023, Pacaso was recognized as a Best Workplace in the Bay Area™, and in 2022, it ranked among the Best Medium Workplaces™, Best Workplaces for Real Estate™, and Best Workplaces for Millennials™. Additionally, Pacaso was ranked #6 on Glassdoor's 2022 list of Best Places to Work and was one of LinkedIn's top startups in 2022.

Overview

The Director of Owner Experience owns the end-to-end ownership journey across the Pacaso portfolio — ensuring every owner interaction reflects a seamless, responsive, and premium experience.

This leader oersees a two-tier organization of Owner Experience Managers (regional lifecycle and retention leaders) and Owner Experience Agents (24/7 support and issue resolution). The Director is accountable for experience strategy, retention performance, resale governance, and cross-functional alignment.

This is a luxury experience, retention, and operations leadership role — not a call center position.

What You Own

Owner Experience Strategy & Lifecycle

  • Define and evolve the ownership journey from post-sale onboarding through active ownership and resale
  • Establish service principles aligned with Pacaso’s luxury brand and high-net-worth expectations
  • Serve as the executive steward of the owner voice across the organization

Organizational Leadership

  • Lead and develop a team of Owner Experience Managers and Agents
  • Ensure clear role differentiation:
    • Managers: regional relationship ownership and retention strategy
    • Agents: 24/7 intake, issue resolution, and in-stay support
  • Build hospitality-grade training, coaching, and quality standards
  • Drive performance through measurable expectations and accountability

Retention, Utilization & Owner Health

  • Own portfolio-level retention and engagement strategy
  • Define leading indicators of churn risk and utilization gaps
  • Implement proactive intervention frameworks to protect long-term owner value
  • Partner with Sales on resale prevention and transition strategy

 

Resale Strategy & Transaction Oversight

  • Own the strategy and governance for resale listings across the Pacaso portfolio
  • Establish pricing frameworks, listing standards, and share positioning guidance in partnership with Sales
  • Ensure Managers are equipped to advise owners on resale pricing, timing, and expectations
  • Oversee resale workflows, contract execution standards, and transition coordination
  • Protect brand integrity and owner sentiment throughout resale and offboarding

Service Delivery & Operational Excellence

  • Oversee 24/7, multi-channel service delivery across phone, chat, text, email, and AI-supported channels
  • Define SLAs, escalation standards, and resolution frameworks
  • Ensure peak-season and crisis response models protect owner trust
  • Balance operational efficiency with luxury service standards

Asset Management & Field Partnership

  • Define and formalize workflows between Owner Experience (relationship & communication) and Asset Management (field execution & home readiness)
  • Ensure clear accountability from intake → field execution → resolution
  • Own communication, follow-through, and service recovery; partner with Asset Management on physical remediation
  • Eliminate friction between owner expectations and on-the-ground delivery

 

Performance, Systems & Governance

  • Own key metrics including CSAT, retention, utilization, escalation trends, and resolution quality
  • Manage budget, headcount planning, and executive reporting
  • Partner with Product and Engineering to enhance CRM visibility, AI capabilities, and owner data insights
  • Continuously refine workflows, tooling, and performance standards to scale the function

Ideal Profile

  • 10–15+ years of leadership experience in luxury hospitality, high-end property management, private membership, luxury real estate, or comparable high-touch environments
  • Director-level ownership of end-to-end client or owner experience across a long-term lifecycle
  • Proven leader of a 24/7, multi-channel service organization with escalation and crisis accountability
  • Experience supporting high-value clients through complex operational, financial, and ownership-related conversations
  • Strong understanding of real estate listing strategy, pricing dynamics, and transaction processes, including resale coordination and contract oversight
  • Track record of building hospitality-grade teams measured by satisfaction, retention, and lifetime value
  • Strong operational and financial acumen; data-driven, decisive, and comfortable influencing at the executive level
  • Background in brands such as Four Seasons, Ritz-Carlton, Rosewood, Aman, Inspirato, Exclusive Resorts, private residence clubs, or comparable ultra-luxury hospitality or ownership environments preferred

 

Compensation Estimate

  • $150-170k with equity (RSU)

You’ll love working at Pacaso because of our ...

  • Competitive salary and stock options.
  • Unlimited, flexible PTO for exempt employees.
  • Excellent medical, dental and vision insurance.
  • Sponsored memberships to One Medical, Ginger and Carrot.
  • 401(k) to help you save for the future.
  • Paid maternity and paternity leave.
  • Generous home office stipend and monthly cell phone reimbursement.
  • Quarterly remote team building events and L&D opportunities.

Pacaso encourages applications from people of all races, religions, national origins, genders, sexual orientations, gender identities, gender expressions and ages, as well as veterans and individuals with disabilities.     

 

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