RRE Portfolio Careers

Chief Operating Officer (COO)

Location: Long Island, NY (Hamptons)
Company: Winner Hospitality (Outpost Location)

Employment Type: Full-Time, Exempt

Salary Range: $125,000 - $150,000

Reports To: Ownership and General Manager

About the Role

Winner is seeking an experienced, hands-on Chief Operating Officer (COO) to oversee day‑to‑day operations for a high‑volume, hospitality‑driven outpost located in the Hamptons. This is a senior leadership role responsible for translating ownership vision into consistent execution across food, beverage, retail, and guest experience.

The ideal candidate is operationally rigorous, calm under pressure, deeply familiar with hospitality systems, and comfortable working directly with ownership and on‑site leadership. This role partners closely with the General Manager and serves as a key decision‑maker for the business.

Key ResponsibilitiesOperations & Execution

• Oversee all daily operations of the outpost, ensuring seamless execution across departments
• Partner with the General Manager to drive operational excellence and accountability
• Establish, refine, and enforce SOPs across service, production, retail, and facilities
• Ensure consistent guest experience aligned with Winner standards
• Identify operational gaps and implement scalable solutions

Financial Oversight & Performance

• Monitor and manage P&L performance in collaboration with ownership and finance partners
• Oversee labor management, scheduling strategy, and productivity benchmarks
• Analyze sales, margins, and costs; recommend adjustments to improve profitability
• Support budgeting, forecasting, and seasonal planning
• Maintain strong controls around cash handling, inventory, and purchasing

Leadership & Team Development

• Lead, support, and mentor the General Manager and department leaders
• Build a culture of accountability, professionalism, and continuous improvement
• Support hiring, onboarding, training, and performance management at the leadership level
• Act as a coach and problem‑solver during peak season and high‑pressure periods

Guest Experience & Brand Stewardship

• Uphold Winner’s standards for hospitality, food quality, and retail presentation
• Address escalated guest concerns with empathy and decisiveness
• Ensure the outpost reflects the brand’s values, tone, and aesthetic
• Collaborate with marketing and ownership on special events, seasonal activations, and brand moments

Compliance, Safety & Risk Management

• Ensure compliance with all local, state, and federal regulations
• Oversee food safety, health department readiness, and licensing requirements
• Partner with HR to ensure labor law compliance and best practices
• Proactively identify operational, safety, or reputational risks

Qualifications

• 7+ years of senior operations leadership in hospitality, food retail, or multi‑unit food service
• Proven experience overseeing complex, high‑volume operations
• Strong financial acumen with hands‑on P&L responsibility
• Demonstrated ability to lead managers and influence culture
• Comfortable working directly with owners and senior stakeholders
• Highly organized, decisive, and solutions‑oriented
• Willingness to be present on‑site, especially during peak seasonal periods

Work Environment & Schedule

• Seasonal intensity with increased hours during peak Hamptons season
• Combination of strategic oversight and hands‑on operational support
• On‑site presence required

Why Join Winner

• Opportunity to play a pivotal leadership role in a flagship outpost
• Direct collaboration with ownership and senior leadership
• Ability to shape systems, culture, and long‑term success
• Competitive salary
• Performance-based bonuses
• Health insurance
• Paid time off
• 30% employee discount
• Housing Support*

* For candidates relocating to the Hamptons area, Winner may offer housing support or assistance, subject to availability and individual circumstances. Any housing arrangement would be discussed during the offer stage and structured separately from base compensation.

Winner is an equal opportunity employer. We value diverse backgrounds, experiences, and perspectives and are committed to building an inclusive workplace.