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Director of Operations and Strategy

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.

About the Role / The Opportunity: 

We are seeking a dynamic and strategic Director of Operations and Strategy to join the Pacaso Operations team. This role is ideal for a systems thinker and builder — someone who can lead large-scale initiatives, drive operational excellence, and partner cross-functionally to develop high-impact solutions.

This leader will act as an internal consultant across the Operations org, owning critical projects that enhance how our teams operate and serve Pacaso’s owners. Their first focus will be the leadership and development of our Central Support team — a 24/7 service team that plays a vital role in delivering world-class support to our owners. Over time, the role will evolve to take on new strategic projects across departments that have a critical impact on core business objectives. 

What You Will Do (Responsibilities):

Phase 1: Lead and Develop the Central Support Team

  • Support the development and execution of a scalable strategy for a 24/7/365 global service team that supports both Pacaso owners and internal crew members.
  • Define and articulate a clear vision and multi-quarter strategic plan, ensuring its evolution aligns with broader company objectives and anticipated owner needs.
  • Oversee a high-performing team of managers, specialists, and contractors, with a focus on training, system and process implementation. 
  • Manage the Central Support budget and resourcing plan - this includes developing staffing models. 
  • Optimize workflows and implement SOPs to improve service quality and efficiency.
  • Capture customer feedback and operational data to inform decisions and share actionable insights with cross-functional partners.
  • Collaborate with Product, Engineering, Market Operations, and Marketing to shape policies, build systems, launch new tools and develop AI-driven solutions - including the launch of Pacaso’s new In App AI Concierge.  
  • Develop and enforce policies that ensure a safe, reliable, and empathetic support experience for all owners.
  • Define and report on key metrics and SLAs to ensure high-quality service and accountability across Central Support operations.

Phase 2 and Beyond: Drive Strategic Operations Projects

  • Own the end-to-end strategy and execution of high-impact initiatives related to owner experience, operational efficiency, and business model evolution. Drive alignment across leadership, secure executive buy-in, and deliver measurable outcomes.
  • Build strong partnerships across Finance, Product, Engineering, Sales, Market Operations, Capital Projects, and other teams to design and implement scalable systems, tools, and workflows that improve overall operational performance.
  • Act as a trusted strategic advisor to senior leadership, providing data-driven insights, critical analysis, and operational recommendations that shape company priorities and resourcing decisions.
  • Develop, implement, and refine scalable operational frameworks, SOPs, dashboards, and decision-support tools that increase visibility, alignment, and productivity across operational functions.
  • Expertly manage complex trade-offs and make sound, timely decisions throughout the lifecycle of strategic initiatives, ensuring objectives are met even under pressure or with ambiguity.
  • Champion the development of business intelligence and data infrastructure within Ops. 
  • Lead user research and field engagement to deeply understand crew, owner, and partner needs—and translate insights into scalable solutions.
  • Identify key risks to execution and build mitigation strategies to protect timelines, budgets, and service outcomes.

About you:

  • 8–10+ years of experience in operations, strategy, or a related field, preferably in a high-growth or tech-enabled environment or business consulting. 
  • Demonstrated expertise in structured problem-solving, project/program management methodologies, and developing/implementing strategic recommendations in complex environments (consulting experience highly valued).
  • Proven leadership experience, including direct people management and cross-functional influence.
  • Exceptional analytical, quantitative, and systems-thinking skills, with proven ability to develop models, conduct complex analyses, and translate data into actionable strategic recommendations.
  • Experience standing up or overhauling customer support or service delivery functions.
  • Demonstrated success leading complex projects from ideation through implementation.
  • Excellent communication and stakeholder management skills, especially in a distributed/remote environment.
  • Ability to synthesize complex information into clear, concise, and compelling narratives, plans, and presentations tailored for executive-level decision-making.
  • Deep experience working with product, engineering and/or U/XAbility to see the big picture and focus on the smallest details in operations; you're a systems thinker who loves getting in the weeds. 
  • You’re a team player and always focus on the greater good.

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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