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Chief Operating Officer (COO)
Chief Operating Officer (COO)Rogers Park Montessori School • Chicago, IL, United States
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Chief Operating Officer (COO)

Chief Operating Officer (COO)

Rogers Park Montessori School • Chicago, IL, United States
14 days ago
Job type
  • Full-time
Job description

Position Summary

Rogers Park Montessori School, serving 340 students and employing approximately 75 faculty and staff, seeks its next Chief Operating Officer (COO), a key member of the senior leadership team responsible for overseeing and aligning core operational functions to ensure the organization's programs and services are delivered effectively, efficiently, and with a strong focus on compliance and continuous improvement. An ideal candidate will ensure that operational excellence enables the school’s mission and Montessori principles to thrive.

This includes leading cross-functional project management initiatives, managing the organization’s HR systems and processes, overseeing IT infrastructure and vendors, and supporting financial strategy in partnership with the CFO or Finance Director.

This role requires a strategic thinker with strong execution skills and the capability of translating organizational goals into actionable operational plans. The ideal candidate will be detail-oriented, systems-minded, and experienced in nonprofit operations.

Key Responsibilities

Project Management (Strategic and Cross-Functional)

  • Lead organization-wide project planning, implementation, and tracking.
  • Coordinate cross-departmental initiatives to improve efficiency and accountability.
  • Develop and maintain dashboards and tools to monitor project timelines, milestones, and outcomes.
  • Standardize project management methodologies and build staff capacity for project execution.
  • Manage the collaboration between IT, Office Operations, and Program Teams, optimizing for efficiency and clarity of communication

Human Resources Administration (Technical Oversight)

  • Oversee the implementation and optimization of HRIS and payroll systems, particularly the digitization and maintenance of employee-facing portals
  • Liaise with school counsel to ensure compliance with employment laws, benefits administration, and internal policies.
  • Develop and manage HR processes related to onboarding, performance evaluations, and employee data reporting.
  • Supervise or liaise with external HR consultants and / or internal HR staff

    • Operations Management

  • Manage cross-departmental processes such as lifecycles, dashboards, and workflows to ensure alignment and continuity
  • Regularly review and update standard operating procedures
  • Coordinate and supervise IT, Office Operations, and Management to ensure mutual awareness, alignment of priorities, and thorough follow-through on outstanding action items.
  • Support each department in developing OKRs and monitor quarterly, in concert with the Principal
  • Manage risk management processes, including annual processes for assessing risk and ensuring robust security protocols

    • Information Technology Oversight

  • Manage the organization’s IT infrastructure in partnership with a consultant.
  • Lead the development of IT policies, procedures, and training initiatives.
  • Oversee systems integration, data security, and user support.

    • Evaluate and recommend technology solutions aligned with programmatic and operational needs.

    Finance Strategy Support

  • Collaborate with the Director of Finance and the Principal to align operational priorities with financial goals.
  • Contribute to annual operational budget development through scenario planning.
  • Monitor cost-efficiency in operational departments and vendor contracts.

    • Qualifications

  • 8+ years of progressive operational leadership experience, ideally in a nonprofit or mission-driven organization.
  • Proven track record of successful cross-functional project management.
  • Strong working knowledge of HR compliance, systems, and reporting tools.
  • Experience managing IT systems and working with third-party technology vendors.Familiarity with nonprofit financial principles; ability to interpret financial statements and budgets.
  • Excellent communication, analytical, and organizational skills.
  • Collaborative leadership style with an ability to work across diverse teams.

    • Preferred Qualifications

  • PMP or similar project management certification.
  • Experience with systems such as ADP, Paylocity, QuickBooks, Salesforce, or Microsoft 365.
  • Prior experience supporting leadership in strategic planning or change management.

    • Work Environment

    This position is 100% in-person, on campus.

    Equal Opportunity

    Rogers Park Montessori School is an Equal Opportunity Employer and encourages applicants from all backgrounds to apply, especially individuals from historically underrepresented communities.

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