Chief of Staff

Proper Hospitality Careers•Santa Monica, CA

7d•Onsite

About The Position

Proper Hospitality is hiring a Chief of Staff to work directly with its CEO and President, reporting jointly to both. The role is designed to improve the effectiveness of the founders and leadership team by anticipating decisions, providing independent judgment and recommendations, focusing the organization on its highest priorities, and helping work move forward. It is an entrepreneurial position requiring strategic thinking, business judgment, and the ability to influence across the organization. The COO remains responsible for day-to-day operations; the Chief of Staff manages the founders’ strategic agenda and leadership priority and OKR process, and partners with the COO on cross-functional matters. The position focuses on strategy and founder leverage, leadership priorities and accountability, cross-functional initiatives, and AI and technology oversight and transformation. The Chief of Staff will help identify risks and opportunities, support major business decisions, improve executive meetings and decision-making, establish clear priorities and accountability, and launch selected initiatives with defined owners and handoff plans. The role is not a second COO, permanent project manager, technology developer or systems operator, or process-driven administrative position. The Chief of Staff is expected to be a sophisticated daily user of AI and help leaders identify and prioritize useful applications, support adoption, and ensure initiatives have clear ownership, cost discipline, and measurable results. The position also requires meaningful time at Proper properties to build relationships with hotel teams and understand operational challenges and opportunities. The role is based full-time at the Los Angeles corporate headquarters, with regular travel to hotels.

Requirements

7 to 15 years of experience 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, including 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 helping teams adopt new ways of working.
Ability to turn ambiguous problems into practical solutions, engage the right people, and see changes through to implementation.
Strong executive communication skills, 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 is useful.
Ability to work effectively with two founders while maintaining a shared agenda.
Willingness to work in person at the Los Angeles headquarters and regularly visit hotels.

Nice To Haves

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.

Responsibilities

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.
Help ensure founders’ time is focused on high-value priorities and that they have the information needed to decide efficiently.
Maintain a shared understanding of founders’ priorities and help align them on company and leadership-team focus.
Support analysis of growth opportunities, new developments, partnerships, and other important business decisions.
Partner with founders, the 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.
Identify slipping progress, unclear ownership, and competing priorities, and work with leaders to resolve them.
Improve executive meetings by surfacing the right issues, preparing discussions, and ensuring decisions conclude with clear next steps.
Build alignment around new priorities and ways of working, motivate people, work through resistance, and promote accountability without unnecessary process.
Identify, frame, and launch selected cross-functional initiatives, translating objectives into priorities, success measures, timelines, and ownership.
Bring stakeholders together, remove early obstacles, create momentum, track progress, and escalate meaningful issues.
Ensure each initiative has a named business owner and that execution is handed to a permanent leader rather than retained by the Chief of Staff.
Take on selected special projects aligned with founders’ priorities, with clear objectives, accountability, and a defined handoff plan.
Help founders and executives identify and prioritize high-value AI and technology opportunities.
Partner with technology, data, finance, and functional leaders to give AI and technology initiatives clear objectives, business ownership, cost discipline, and measurable results.
Support AI adoption by helping leaders understand capabilities and incorporate AI into their work.
Evaluate new technology capabilities based on business value, organizational readiness, and implementation complexity.
Spend meaningful time at properties, build relationships with general managers and hotel teams, and surface issues and opportunities not visible in corporate reporting.
Ensure corporate initiatives reflect hotel operations and Proper’s approach to hospitality.

Benefits

Performance-based bonus.
Medical, dental, and vision plans through Aetna.
Company-subsidized Equinox and ClassPass memberships, wellbeing workshops, and mental health resources.
Employee Assistance Program through Unum, including emotional wellbeing, financial planning, and life management support.
Flexible paid time off and 11 paid holidays each year for corporate team members.
Paid parental leave for eligible employees welcoming a child through birth, adoption, or foster placement.
Flexible work practices for eligible roles.
401(k) with a company match of 50% of employee deferrals, up to the first 4% of eligible compensation.
Employer-paid life and disability insurance, with optional additional coverage.
Financial education tools and workshops.
Hotel stays at 75% off BAR, with a $100 floor, across the Proper portfolio.
50% off participating Marriott Design Hotels.
75% off food and beverage at Proper Hospitality outlets.
Complimentary or subsidized parking, cell phone reimbursement, and hospitality and retail discounts.
Access to training, leadership programs, mentorship, and cross-property mobility.
Opportunities for community volunteerism, sustainability, and charitable partnerships.