Director Chief Operating Officer Insurance Jobs in Chicago, IL

Salary Range: $170,000.00 To $175,000.00 Annually

Reports to: Chief Executive Officer

Location: Chicago, IL (hybrid with regular on-site presence)

Classification: Full-time, exempt

The Chief Operating Officer (COO) is a senior executive leader responsible for translating organizational strategy into effective, mission-aligned operations. Reporting to the CEO, the COO oversees the people, systems, and infrastructure that support programmatic excellence, financial sustainability, and a strong workplace culture.

The COO provides executive oversight of core operational functions, including human resources, compliance and risk management, facilities, and organizational infrastructure. The role also includes oversight of organizational safety and security, ensuring that protocols and physical measures are proactive, well-communicated, and responsive to evolving risks.

• Serve as the CEO’s primary partner on operational strategy and execution.
• Serve as key decision-maker over day-to-day operational functions, ensuring timely and effective execution across departments.
• Translate the organization’s multi-year strategic plan into operational priorities, milestones, and performance metrics.
• Ensure cross-departmental alignment and accountability for operational outcomes.
• Identify and implement improvements to systems, workflows, and internal processes.
• Serve as a liaison to the board, fostering the board’s understanding of the agency’s mission and programs.
• In partnership with the CFO, oversee the organization’s operating budget, identify risks or variances, and recommend corrective actions.
• Maintain fluency in staffing models and personnel costs to ensure efficient and sustainable operations.
• Support long-term planning related to growth, capacity, and resource allocation.

• Provide executive-level oversight of human resources and people operations, in partnership with the HR Director.
• Ensure effective implementation of employee benefits, policies, and performance management systems.
• Partner with senior and center leadership to strengthen staff engagement, retention, and organizational culture.
• Support leadership transitions and succession planning across operational and center teams.

• Provide executive oversight of organizational safety and security across all sites.
• Ensure effective implementation and regular review of security protocols, emergency preparedness plans and physical safety measures.
• Oversee relationships with external security partners, consultants and relevant agencies, in partnership with Director of Risk Management.
• Oversee organizational compliance with regulatory, licensing, and employment requirements.
• Manage risk management strategy, including insurance coverage, audits, and incident response.
• Serve as the primary liaison to insurance brokers and compliance partners.

• Oversee facilities management, capital projects, and long-term maintenance planning, in partnership with the Director of Facilities.
• Provide executive oversight of IT systems, data security, and operational technology.
• Ensure infrastructure supports safe, effective, and scalable operations.
• Maintain strong relationships with vendors related to facilities, technology, and operational services.

• Directly supervise senior operational leaders, including:
  • Directors of City and Suburban Experience
  • Director of Facilities
  • Director of Risk Management
  • HR Director
• Foster a culture of collaboration, accountability, and continuous improvement, while coaching and developing operational leaders.

• Bachelor’s degree in Business Administration, Operations, or related field.
• 10+ years of progressive leadership experience in operations, preferably in a nonprofit, education, or mission-driven organization.
• Demonstrated success overseeing and supervising complex operational functions, including HR, facilities, and budget management.
• Strong understanding of people operations, employment practices, and organizational culture.
• Proven ability to lead through change with clarity, empathy, and decisiveness.
• Exceptional judgment, discretion, and emotional intelligence.

• Experience in early childhood education, education, or human services.
• Familiarity with multi-site operations.
• Experience leading during periods of organizational transition or growth.
• Ability to develop and coach talent across multiple career stages.
• Knowledge of Chicagoland Jewish community.

The ideal candidate will be:

• Collaborative and people-centered, with high emotional intelligence
• A clear, skilled communicator
• Systems-oriented and detail-driven, without losing sight of the big picture
• Comfortable making decisions in complex, nuanced environments
• Aligned with the organization’s mission, values, and community-based culture
• Skilled at navigating complex relationships with diplomacy, professionalism, and sound judgment