Job Description

Proper Hospitality is a growing collection of luxury lifestyle hotels that blend design, culture and a deep sense of place. As we expand, we’re hiring a Chief of Staff to support the CEO and President as a strategic partner and operational lead.

This is a cross-functional role focused on driving strategic initiatives, improving decision-making and supporting coordination across the company. It’s part operator, part analyst, part advisor. The ideal candidate will possess a unique blend of leadership 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

Technology & AI Enablement

Proper has already taken significant steps to integrate AI across key areas of the business—from labor forecasting and guest personalization to back-of-house automation. We’re looking for a strategic leader to build on this momentum and scale what’s working.

In this role, you will:

• Identify and champion high-impact AI applications that enhance operations, communication, and decision-making across the organization
• Oversee the implementation of tools, vendors, and pilots—no coding required, but you’ll need the fluency to lead effective evaluations and deployment
• Drive cross-functional innovation and help institutionalize AI as a core capability that reinforces Proper’s leadership in applied AI
• Lead the execution of Proper’s AI-first operations strategy—continuously optimizing labor, enriching the guest experience, and improving forecasting accuracy across the portfolio

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.

Why This Role Matters 

This is a key leadership role at the center of a growing company. You’ll be involved in shaping how Proper evolves, scales, and performs. You’ll work directly with founders, and your input will influence the direction of the business.

Company Overview

Proper Hospitality is a diverse team 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 the best of the best—both within and outside the industry—to join us in building a new kind of lifestyle hospitality company, inspired by a centuries-old tradition. We’re a small, focused team building something long-lasting. The work is hands-on, dynamic, and meaningful.

To achieve our vision—to inspire and transport people—we seek like-minded candidates who embody our ethos, The Pillars of Proper:

• Care Proper: We are natural and gracious hosts to all.
• Achieve Proper: We are committed to excellence.
• Imagine Proper: We are resourceful.
• Present Proper: We have an appreciation for style and culture.

Proper Hospitality is an equal-opportunity employer. We provide employment opportunities to all individuals regardless of race, color, religion, sex, national origin, age, disability, gender identity or expression, genetics, or any other federally or state-protected category.

We also consider qualified applicants with criminal histories in accordance with local Fair Chance Hiring Ordinances.

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