Proper Hospitality is a distinguished collection of luxury lifestyle hotels, combining refined elegance, innovative design and unparalleled guest experiences. We are redefining luxury travel by offering distinctive stays that celebrate both sophistication and local culture. As we continue to expand, we are seeking a Chief of Staff to serve as a trusted advisor and strategic partner to both our Chief Executive Officer and President.

This role combines high-level operational oversight with deep analytical capabilities to drive strategic initiatives, enhance decision-making and ensure seamless coordination across departments. The ideal candidate will possess a unique blend of leadership, strategic thinking and data-driven analytical expertise, ensuring Proper Hospitality’s sustained growth and exceptional service delivery.

Key Responsibilities:

Strategic Leadership

• Collaborate closely with the CEO and President to define and implement Proper Hospitality’s strategic vision and objectives
• Lead cross-functional strategic initiatives, ensuring alignment with organizational goals and timelines
• Monitor industry trends, competitor strategies and market dynamics to provide actionable insights for leadership

Analytical Excellence

• Collaborate with team members across Proper Hospitality to strengthen the analytics function, ensuring complex data is translated into clear, actionable insights that drive informed decision-making
• Work closely with departmental leaders to refine and implement performance metrics, KPIs and dashboards that align with organizational goals
• Partner with teams to conduct financial and operational analyses, identifying opportunities to enhance efficiency, foster growth and improve profitability

Executive Support & Coordination

• Serve as a key point of contact and advisor to the executive leadership team, facilitating communication and collaboration
• Manage the executive office’s daily operations, including agenda-setting, meeting preparation, and follow-up on key action items
• Represent the CEO and President in internal and external meetings, ensuring alignment with organizational priorities

Organizational Effectiveness

• Drive the execution of key initiatives, ensuring all stakeholders are informed and accountable
• Develop frameworks and processes to improve decision-making, resource allocation and organizational efficiency
• Act as a culture ambassador, promoting collaboration, innovation and excellence across all teams

Stakeholder Engagement

• Build and maintain strong relationships with internal and external stakeholders, including investors, partners and clients
• Act as a liaison between the executive team and department leaders to ensure alignment on priorities and strategies

Qualifications:

• Education: Bachelor’s degree in Business Administration, Hospitality Management, Economics, or a related field. Master’s degree (e.g., MBA) strongly preferred
• Experience: Minimum 7-10 years of experience in strategic planning, business analytics or a leadership role within the luxury hospitality or related industry
• Proven experience in a consulting role, ideally with a leading consultancy or top-tier firm
• Proven track record of managing complex projects and cross-functional teams
• Exceptional analytical skills, with proficiency in data visualization tools (e.g., Tableau, Power BI) and advanced Excel
• Strong financial acumen, including experience with P&L management and ROI analysis
• Experience within the hospitality industry preferred but not required

Skills and Competencies:

• Strategic thinker with exceptional problem-solving and decision-making abilities
• Outstanding communication and interpersonal skills, with the ability to influence and inspire stakeholders at all levels
• Highly organized, detail-oriented, and capable of managing multiple priorities in a fast-paced environment
• Passion for the luxury hospitality industry and a commitment to delivering exceptional guest experiences
• High emotional intelligence (EQ) and the ability to navigate complex organizational dynamics

Work Environment:

This position is based at the corporate headquarters with occasional travel to the hotel portfolio and partner sites. Flexibility to adapt to the demands of a dynamic and fast-growing organization is essential.

Company Overview

Proper Hospitality is made up of a diverse group of passionate individuals who share a common love for hotels and the art of hospitality. Our philosophy is simple: There is a right way to do things and anything less just isn’t proper. We are seeking out the “best of the best” from inside and outside of the industry to work alongside us as we grow a new kind of lifestyle Hospitality Company inspired by a centuries-old tradition. The work is challenging and fast-paced, but rewarding above all.

We provide equal employment opportunities to all employees and applicants for employment without regard to race, color, religion, sex, national origin, age, disability, genetics, or any other federal/state protected category.

Proper Hospitality will consider qualified applicants with criminal histories in a manner consistent with local Fair Chance Hiring Ordinances.