Director of Operations and Strategy

Summary

Join Pacaso as their dynamic Director of Operations and Strategy! Lead and develop their 24/7 Central Support team, focusing on scalability and world-class owner support. Develop a multi-quarter strategic plan aligned with company objectives. Oversee a high-performing team, manage budgets, optimize workflows, and implement SOPs. Collaborate cross-functionally to build systems and AI-driven solutions. Beyond the initial phase, lead strategic operations projects impacting owner experience and business model evolution. Build strong partnerships across departments, act as a strategic advisor to senior leadership, and develop operational frameworks. Champion business intelligence and data infrastructure, conduct user research, and mitigate execution risks. This role requires 8+ years of experience in operations or strategy, proven leadership, exceptional analytical skills, and experience with customer support functions.

Requirements

• 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/X
• Ability 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

Responsibilities

• 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
• 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

Benefits

• 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