Senior Director Human Resources

CSS seeks a Senior Director of Human Resources to lead and modernize its HR function in direct support of the organization’s mission. This is a senior leadership opportunity for an experienced HR professional who brings strategic vision, operational depth, and a genuine commitment to equity—someone who understands that strong people infrastructure is what enables a mission-driven organization to do its best work in the world.

The Senior Director will report to the Vice President for Administration and lead a team of four direct reports:
Associate Director, Human Resources Manager, Senior Manager HRIS and Payroll, and HR Administrator.

The Senior Director will align organizational strategy with resources to build a high functioning HR department, establishing processes that reinforce accountability, codify best practices, and produce measurable outcomes. The successful candidate will have a proven track record across the full HR generalist spectrum—talent acquisition, employee engagement, benefits administration, performance management, and compensation—and will serve as a strategic partner to the Vice President for Administration and Leadership Team.

Experience in a unionized environment is strongly preferred.

• Align strategy with resources to meet CSS’s HR goals and build an effective and forward-looking HR department.
• Establish processes that drive staff accountability, clearly defined goals, and measurable objectives in support of CSS’s performance-focused culture.
• Provide strategic HR counsel to the VP for Administration and senior leadership on workforce and organizational matters.

• Review, evaluate, and institutionalize consistent processes for recruiting, onboarding, benefits administration, professional development, training, performance management, and compensation.
• Ensure clear communication and transparency of HR processes, including timely and official communication of HR decisions throughout the organization.
• Update and maintain CSS’s employee handbook to provide staff with current, accurate information on benefits, policies, and procedures.
• Maintain current knowledge of NYC, NYS, and federal employment regulations and ensure organizational compliance.

• Coordinate and implement best practices across recruitment, retention, and development, including policies that reflect CSS’s commitment to equity.
• Lead and support in building a robust talent pipeline aligned with organizational needs.
• Champion learning and development efforts that build staff capacity and support CSS’s performance review and compensation cycles.
• Provide oversight and management of outside providers, including payroll, insurance, recruitment, employee benefits, and retirement.
• Lead provider negotiations and manage relationships with external consultants in pension administration, defined benefit plans, personal leave, workers’ compensation, and employee benefits.
• Lead accurate and timely benefits administration and related communication to staff.
• Coach and mentor a team of four HR direct reports, serving as a manager, thought partner, and model of HR excellence.
• Build strong internal relationships with the Leadership team and program leaders throughout CSS.
• Foster a collaborative, service-oriented HR team culture that reflects CSS’s values.

• Handle employee relations matters, working closely with GC and other leaders to reach resolution.
• Participate in labor-management meetings, and leading or supporting collective bargaining processes.
• Ensure HR practices are consistent with applicable collective bargaining agreements and law.

• Minimum 10 years of progressive HR experience, with at least 3–5 years in a senior HR leadership role; nonprofit or mission-driven organization experience strongly preferred.
• Bachelor’s degree in HR, Organizational Development, or a related field required; advance degrees and certifications preferred.
• Broad HR generalist expertise across talent acquisition, employee engagement, learning and development, benefits, compensation, performance management, and HRIS.
• Proven ability to build or…