Director of Human Resources

About the role

The Millennium Knickerbocker Hotel Chicago—one of the city's most iconic historic properties—is seeking a highly experienced Director of Human Resources to lead all aspects of the people strategy within a complex, unionized hospitality environment. This role serves as a key member of the Executive Committee, acting as a strategic advisor to the General Manager and leadership team while ensuring operational excellence, compliance, and a highly engaged workforce.

Key Responsibilities

• Serve as the primary liaison with union partners, including Local 1 and Local 399
• Administer and interpret collective bargaining agreements (CBAs) and ensure property-wide compliance
• Lead grievance investigations, disciplinary processes, and arbitration preparation
• Represent management in grievance meetings and support arbitration proceedings
• Partner with legal counsel on labor strategy, compliance, and risk mitigation
• Support collective bargaining negotiations and union information requests
• Act as a trusted advisor to the General Manager and department leaders on workforce strategy and organizational effectiveness
• Align HR initiatives with operational, service, and financial objectives
• Drive a high-performance culture focused on accountability, engagement, and service excellence
• Lead complex employee relations matters, workplace investigations, and conflict resolution
• Oversee performance management and disciplinary consistency across union and non-union associates
• Coach leaders on employee performance, documentation, and corrective action
• Champion engagement initiatives that improve retention, morale, and workplace culture
• Foster a culture of inclusion, respect, accountability, and operational excellence
• Ensure compliance with all federal, state, and local employment laws and regulations, including:
• Chicago Fair Workweek Ordinance
• Illinois labor laws
• Federal wage and hour regulations
• Ensure the integrity of HR systems, personnel records, reporting, and documentation
• Oversee audits, unemployment claims, workers' compensation matters, and legal responses
• Ensure policy consistency and proactive risk management across the property
• Lead recruitment strategy across all hotel departments
• Drive succession planning, leadership development, and internal mobility
• Implement training initiatives aligned with brand standards and operational needs
• Analyze turnover trends and develop retention strategies to improve workforce stability
• Support long-term talent pipeline development for key operational roles
• Payroll & Benefits Oversight
• Ensure payroll accuracy for both union and non-union associates
• Oversee benefits administration and vendor relationships
• Partner with Finance on labor reporting, forecasting, and cost management
• Monitor labor expenses and identify opportunities for operational efficiency

Requirements

• Minimum 8-12 years of progressive Human Resources leadership experience, preferably in hospitality
• Direct union labor relations experience required
• Experience with Local 1 and/or Local 399 strongly preferred
• Demonstrated success managing grievances, arbitration, investigations, and labor compliance
• Strong working knowledge of Chicago labor regulations, ordinances, and union environments
• Proven ability to influence senior leadership and drive organizational results
• Exceptional interpersonal, communication, negotiation, and problem-solving skills
• Bachelor's degree in Human Resources, Business Administration, or related field preferred
• HR certification (PHR, SPHR, or SHRM-CP/SCP) preferred