Founders’ Strategy & Execution Lead

Proper Hospitality; Santa Monica (CA); On-site; USD 250,000 - 275,000; Full time

Benefits offered by this job

Health coverage & wellness benefits

Equinox & ClassPass memberships

Hybrid/work flexibility

PTO & holidays

Job summary

Proper Hospitality seeks a Chief of Staff to work directly with our CEO and President, driving strategic priorities and leadership effectiveness. You will oversee the founders’ agenda, OKR processes, and cross-functional initiatives while partnering with the COO on transformation efforts.

You will manage AI-driven insights, prioritize high-impact work at the executive level, and ensure alignment across leadership.

Qualifications

• 7 to 15 years in strategy, business operations, asset management, investing, organizational leadership or a related field
• Exceptional business judgment and financial fluency, including understanding hotel operating performance and owner economics
• Entrepreneurial initiative: finding opportunities, ambiguity and delivering results
• Proven ability to influence senior leaders and drive accountability without direct reporting authority
• 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, turn complicated issues into clear recommendations
• Sophisticated daily use of AI for analysis, research and communication
• Ability to work with two founders while maintaining a shared agenda
• Willingness to work in person at our Los Angeles headquarters and regularly visit our hotels

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
• 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
• 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
• 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 elevate 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

Skills

Strategic thinking

Business judgment

Influence senior leaders

Leadership & accountability

Executive communication

AI fluency

Job description

Proper Hospitality seeks a Chief of Staff to work directly with our CEO and President, driving strategic priorities and leadership effectiveness. You will oversee the founders’ agenda, OKR processes, and cross-functional initiatives while partnering with the COO on transformation efforts.

You will manage AI-driven insights, prioritize high-impact work at the executive level, and ensure alignment across leadership.