Chief of Staff

• Pay or shift range: $250,000 USD to $275,000 USD
  The estimated range is the budgeted amount for this position. Final offers are based on various factors, including skill set, experience, location, qualifications and other job-related reasons.
• Travel Required :
  Yes

Proper Hospitality builds and operates a growing collection of luxury lifestyle hotels, restaurants and residences defined by design, culture, wellness and a strong sense of place, across Proper Hotels, By Proper and The Collective.

The Role
The 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 Responsibility
Time 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 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

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 elevate meaningful issues without taking on permanent responsibility for execution
• Take on select special projects aligned with the founders’…