The RoleThe Chief of Staff works directly with our CEO and President, reporting jointly to both. The job is to make the founders and leadership team more effective: anticipate important decisions, bring independent judgment and recommendations, keep the organization focused on its highest priorities, and make sure the work moves.
This is a highly entrepreneurial role that requires strategic thinking, strong business judgment, and the ability to influence people across the organization.
Our COO runs the company's day-to-day operations. The Chief of Staff manages the founders' strategic agenda and the company's leadership priority and OKR process, and partners closely with the COO on cross-functional matters.
Areas of ResponsibilityTime will vary with business needs, but the role is expected to focus approximately on:
- Strategy and Founder Leverage: 35 to 45%
- Leadership Priorities and Accountability: 30 to 40%
- Cross-Functional Initiatives: 10 to 20%
- AI and Technology Oversight and Transformation: 10 to 20%
These ranges are flexible. The central priority remains founder leverage and leadership effectiveness.
Key ResponsibilitiesStrategy & Founder Leverage- Develop a deep understanding of the company's strategy, financial performance, operating challenges and growth opportunities
- Identify emerging risks, opportunities, bottlenecks and competing priorities before they require urgent founder attention
- Bring independent recommendations to major decisions, including alternatives, trade-offs and assumptions worth challenging
- Make sure the founders' time goes to the highest-value priorities, with the right information in hand to decide efficiently
- Maintain a shared understanding of the founders' priorities, identify competing demands, and help ensure both founders are aligned on where the company and leadership team should focus
- Support analysis on growth opportunities, new developments, partnerships and other important business decisions
Leadership Priorities & Accountability- Partner with the founders, COO and executive team to set and maintain clear organizational priorities
- Manage the leadership priority and OKR process, including quarterly planning, progress reviews and follow-through on commitments
- See where progress is slipping and work with the COO and founders to resolve it
- Identify unclear ownership and competing priorities, and help leadership resolve them
- Make executive meetings more effective: the right issues surfaced, discussions well prepared, decisions ending in clear next steps
- Build alignment around new priorities and ways of working. Know how to motivate people, work through resistance, and make change stick
- Promote accountability without adding unnecessary process
Cross-Functional Initiatives- Identify, frame and launch a select number of important initiatives that require coordination across departments
- Translate broad objectives into clear priorities, success measures, timelines and ownership
- Bring the right stakeholders together, remove early obstacles and create momentum
- Make sure every initiative has a named business owner from the start, with execution moving to that leader
- Track progress and escalate meaningful issues without taking on permanent responsibility for execution
- Take on select special projects aligned with the founders' priorities, with clear objectives, accountability and a defined handoff plan
The Chief of Staff helps important initiatives get defined, aligned and moving. The goal is to set up successful execution, not to become the permanent owner of the work.
AI and Technology Oversight & TransformationProper is actively integrating AI across its business. We expect our Chief of Staff to be a sophisticated daily user of AI and to understand how it can improve organizational effectiveness, operating performance and decision-making.
- Help the founders and executive team identify and prioritize high-value opportunities to apply AI and technology.
- Partner with technology, data, finance and functional leaders so initiatives have clear objectives, business ownership, cost discipline and measurable results.
- Support adoption by helping leaders understand what AI can do and bring it into their work.
- Evaluate new capabilities with a practical view of business value, organizational readiness and implementation complexity.
- Make sure technology initiatives move to permanent owners rather than becoming ongoing Chief of Staff responsibilities.
You should be fluent enough to judge what's real and what isn't. You are not expected to build, operate or manage technology platforms.
Time in the Hotels & Brand Understanding- Spend meaningful time at our properties, building relationships with general managers and hotel teams
- Surface operational challenges, organizational issues and opportunities that don't show up in corporate reporting
- Make sure corporate initiatives reflect how our hotels actually run and Proper's distinctive approach to hospitality
What This Role Is Not- A second COO. The COO and functional leaders remain responsible for day-to-day operations and operating results.
- A permanent project manager. The Chief of Staff sets direction, momentum and accountability, then hands execution to permanent owners.
- A technology developer or systems operator. The AI mandate is prioritization, oversight and adoption.
- A process-driven administrative role. Success is measured by the quality of decisions and results, not by the number of reports, meetings or frameworks created.
Qualifications & ExperienceRequired- 7 to 15 years in strategy, business operations, asset management, investing, organizational leadership or a related field
- Exceptional business judgment and financial fluency, including the ability to understand hotel operating performance, owner economics and the financial implications of strategic decisions
- Entrepreneurial initiative: finding opportunities, working through ambiguity and getting results without extensive direction
- Proven ability to influence senior leaders and drive accountability without direct reporting authority
- A track record of leading organizational change and getting teams to adopt new ways of working
- Ability to take ambiguous problems, develop practical solutions, engage the right people and see changes through to implementation
- Strong executive communication, including the ability to turn complicated issues into clear recommendations
- Sophisticated daily use of AI for analysis, research and communication, with sound judgment about where it helps and where it doesn't
- Ability to work effectively with two founders while maintaining a shared agenda
- Willingness to work in person at our Los Angeles headquarters and regularly visit our hotels
Strongly Preferred- Hotel or hospitality experience, ideally with a management company, ownership group, asset management platform or multi-property operator
- Understanding of hotel operating performance, owner relationships and the economics of an asset-light management business
- Experience working directly with founders, CEOs or senior executive teams
- Genuine appreciation for design, food, culture, wellness and service
How You Work- Judgment: You know what's important versus what's merely urgent, when to escalate, and you bring recommendations, not just problems.
- Leadership and Influence: You build trust, motivate people, and move executives and teams without formal authority.
- Candor: You'll challenge the founders and senior executives constructively when you see a better approach.
- Pragmatism: You focus on what works, not unnecessary process or theoretical solutions.
- Discipline: You spend your time on what matters most to the company, not the work you find most interesting.
- Taste: You understand what makes Proper distinct and the importance of design, culture, wellness and guest experience.
- Humility and Confidence: You can make major contributions without needing to own every initiative or get credit for it.
What Success Looks Like at Six Months- The founders have more capacity for their highest-value work and can point to decisions made earlier or better because of you.
- You've identified several meaningful company-level issues or opportunities before the founders raised them, each with a recommendation.
- The leadership team operates with clearer priorities, stronger accountability and a more effective OKR and decision process.
- Initiatives you helped launch sit with accountable owners and are progressing without your ongoing management.
- AI and technology initiatives have clear ownership, spending discipline and measurable business value.
- You've built credibility with the executive team and key leaders across our hotels.
Ultimately, success means the founders are more effective, the leadership team is better aligned, important problems surface earlier, and the company executes more consistently against its priorities.
Work EnvironmentThis position is based full-time at our Los Angeles corporate headquarters, with regular travel to our hotels.
Reporting & Compensation- Reports jointly to the Chief Executive Officer and President
- Base salary: $250,000 to $275,000, plus performance-based bonus
Proper Perks & BenefitsCulture of Growth & Belonging- Culture of Growth: A collaborative, design-forward environment that values creativity, intelligence, and curiosity - where learning and excellence are a daily practice.
- Guided Skills Development: Access to training, leadership programs, mentorship, and cross-property mobility to encourage achievement and discovery.
- Diversity, Equity, Inclusion & Belonging: We honor individuality while fostering a culture of respect and belonging across all teams.
- Community Engagement: Opportunities to give back through local volunteerism, sustainability, and charitable partnerships.
Health & Wellness- Comprehensive Health Coverage: Medical, dental, and vision plans through Aetna, designed to fit a range of personal and family needs.
- Wellness Access: Company-subsidized memberships with Equinox and ClassPass, plus wellbeing
- workshops and mental health resources.
- Employee Assistance Program (EAP): Confidential support for emotional wellbeing, financial planning,
- and life management through Unum.
Time Off & Flexibility- Paid Time Off: Flexible PTO plus 11 paid holidays each year for corporate team members.
- Paid Parental Leave: Paid time off for eligible employees welcoming a new child through birth, adoption, or foster placement.
- Flexible Work Practices: Hybrid schedules for eligible roles and an emphasis on work-life balance.
Financial Wellbeing & Core Protections- 401(k) Program: Company match of 50% of employee deferrals, up to the first 4% of eligible compensation.
- Employer-Paid Life & Disability Insurance: Core protections with optional additional coverage.
- Financial Education: Access to planning tools and workshops to support long-term stability and growth.
Lifestyle & Travel Perks- Hotel Stay Benefits: 75% off BAR (floor of $100) across the Proper portfolio.
- Design Hotels Partnership: 50% off participating Marriott Design Hotels.
- Dining Discounts: 75% off food & beverage at all Proper Hospitality outlets.
- Lifestyle Perks: Complimentary or subsidized parking, cell phone reimbursement, and exclusive hospitality and retail discounts.
