Regional Managing Director

The Shelborne by Proper is an iconic Miami Beach landmark reimagined through the lens of Proper Hospitality. Set along the ocean in the heart of South Beach, our historic Art Deco property brings together thoughtful design, elevated hospitality, dynamic food and beverage, wellness, nightlife, and a distinctly Miami sense of energy. More than a hotel, The Shelborne is envisioned as a destination for both travelers and locals — honoring the character and history of the property while creating a modern luxury experience that feels deeply connected to the culture, rhythm, and spirit of Miami Beach.

Position Overview

We are seeking an exceptional Regional Managing Director to lead The Shelborne by Proper while providing executive oversight of Montauk Yacht Club, two distinctive luxury destinations within the Proper Hospitality portfolio.

Based in Miami, this role serves as the senior-most executive at The Shelborne and holds direct responsibility for the property’s leadership, performance, and continued evolution as one of Miami Beach’s most distinctive luxury destinations. The Regional Managing Director will also oversee Montauk Yacht Club, partnering closely with its on-property leadership team to guide strategy, strengthen performance, and ensure alignment with Proper Hospitality’s standards and vision.

The Regional Managing Director holds full responsibility for The Shelborne’s financial results, guest experience, operations, food and beverage, nightlife, sales and marketing, and people and culture. Across both The Shelborne and Montauk Yacht Club, this leader will establish clear priorities, develop high-performing leadership teams, identify opportunities for growth, and drive operational and commercial excellence while preserving the distinct identity and sense of place that define each hotel.

What You'll Do

Lead the Business

• Own the overall strategy, performance, and day-to-day leadership of The Shelborne by Proper, while providing executive oversight and strategic direction for Montauk Yacht Club
• Maintain accountability for the financial and operational performance of both properties, including revenue, profitability, labor, expenses, forecasting, and annual budgets
• Partner closely with the on-property leadership team at Montauk Yacht Club to establish priorities, evaluate performance, and ensure strong execution throughout its seasonal operating cycle
• Identify opportunities to grow revenue and profitability across rooms, food and beverage, nightlife, events, wellness, membership, and other ancillary experiences
• Maintain a sophisticated understanding of the luxury hospitality landscapes in both Miami Beach and the Hamptons, anticipating changes in demand, competition, consumer behavior, and market opportunity
• Identify opportunities to share talent, resources, best practices, and commercial strategies across the two properties while respecting the distinct identity and operating needs of each
• Partner closely with Proper Hospitality’s corporate leadership and ownership on long-term positioning, capital priorities, and strategic initiatives across both assets

Build Exceptional Leadership Teams

• Develop and retain a high-performing Executive Committee and senior leadership team at The Shelborne
• Provide guidance, mentorship, and accountability to the on-property leadership team at Montauk Yacht Club
• Develop leaders who are commercially minded, operationally disciplined, and deeply invested in the guest experience
• Maintain a highly visible daily presence at The Shelborne and a meaningful presence at Montauk Yacht Club, particularly during key operating periods
• Create strong communication and operating rhythms across both properties, ensuring priorities, performance expectations, and company standards remain aligned
• Set a high standard for performance while creating environments where talented hospitality professionals want to build their careers
• Strengthen succession planning and leadership development across both hotels, identifying opportunities for talent mobility and shared learning

Deliver the Proper Guest Experience

• Serve as the ultimate steward of service across both properties, ensuring each experience feels elevated, intuitive, personal, and true to its individual identity
• Maintain uncompromising standards across rooms, public spaces, food and beverage, nightlife, wellness, recreation, and every guest touchpoint
• Remain highly connected to guest feedback and property performance, identifying opportunities before they become problems
• Ensure operational excellence never comes at the expense of personality, warmth, creativity, or spontaneity
• Create environments where both first-time visitors and returning guests feel a genuine sense of connection to each property
• Ensure The Shelborne and Montauk Yacht Club each deliver on Proper Hospitality’s standards while retaining the distinct sense of place that makes them compelling destinations

Drive Food, Beverage & Nightlife

• Treat food, beverage, and nightlife as fundamental drivers of each hotel’s identity and business—not simply amenities supporting rooms
• Partner closely with culinary, beverage, nightlife, and corporate F&B leadership to drive performance and continuously evolve the concepts across both properties
• Ensure The Shelborne’s venues, including the Lobby Bar and Little Torch, develop strong identities, loyal local followings, and relevance within Miami’s competitive hospitality landscape
• Support Montauk Yacht Club’s leadership in delivering compelling waterfront dining and social experiences that resonate with resort guests, members, seasonal visitors, and the local community
• Understand the economics of high-volume, seasonal, and experience-driven F&B operations and maintain strong accountability around revenue, labor, cost of goods, and profitability
• Identify opportunities for collaboration, shared programming, and cross-property learning while ensuring each destination maintains its own authentic point of view
• Build environments that attract compelling operators, talent, collaborators, and guests

Steward Community & Cultural Connection

• Serve as one of The Shelborne’s most visible ambassadors within Miami Beach and the broader Miami community
• Support Montauk Yacht Club’s leadership in cultivating meaningful relationships throughout Montauk, the Hamptons, and the broader East End community
• Build relationships across hospitality, art, fashion, entertainment, music, wellness, business, and local cultural communities in both markets
• Partner with brand, marketing, programming, and F&B teams to create experiences and partnerships that feel authentic to each property rather than manufactured
• Ensure programming and partnerships translate into sustained cultural relevance, guest engagement, local loyalty, and commercial value
• Develop strong networks of regulars, tastemakers, partners, members, and community relationships that deepen each property’s connection to its destination
• Represent Proper Hospitality thoughtfully and consistently across both markets

Drive Commercial Performance

• Work closely with Sales, Revenue Management, Marketing, and E-Commerce leadership to maximize market share and overall asset performance across both hotels
• Maintain fluency in key hotel performance metrics, including ADR, occupancy, RevPAR, RevPAR index, flow-through, and profitability
• Understand the customer mix and demand patterns of each property, continually identifying opportunities across leisure, group, corporate, events, local business, membership, and other segments
• Guide strategies that reflect the distinct dynamics of a year-round Miami Beach hotel and a highly seasonal Hamptons resort
• Ensure commercial strategy, operational execution, and brand positioning remain closely connected rather than operating as separate disciplines
• Identify appropriate opportunities for cross-property promotion, customer development, and relationship building
• Balance short-term performance with the long-term value and reputation of The Shelborne, Montauk Yacht Club, and the broader Proper Hospitality portfolio

What We’re Looking For

• Significant senior leadership experience within luxury or high-end independent hospitality
• Previous experience as a Managing Director or General Manager at a complex, high-profile hotel or resort
• Multi-property, regional, or area leadership experience is preferred but not required
• Demonstrated ownership of significant hotel financial performance and a sophisticated understanding of hotel P&L management
• Proven ability to lead one property directly while providing effective executive oversight, strategic direction, and accountability across an additional operation
• Deep operational experience across rooms and food and beverage, ideally within properties where restaurants, bars, nightlife, events, recreation, and seasonal demand are major components of the business
• Experience within both urban lifestyle hotels and resort environments is highly desirable
• Strong commercial instincts and the ability to connect operations, brand positioning, sales, marketing, revenue strategy, and guest experience
• Experience leading large, diverse teams and developing high-performing executive leadership groups
• Genuine understanding of luxury lifestyle hospitality and the expectations of a sophisticated international clientele
• Strong knowledge of—or meaningful connection to—Miami’s hospitality, cultural, entertainment, and lifestyle landscape is highly desirable
• Familiarity with the Hamptons or comparable luxury resort and seasonal markets is preferred
• A highly visible, relationship-driven leadership style and comfort serving as the public face of a property and representative of a broader portfolio
• Proven ability to balance creative ambition with operational discipline and financial accountability
• Exceptional judgment, executive presence, communication skills, and emotional intelligence
• Based in Miami and able to travel regularly to Montauk, particularly during key planning and operating periods