Director of Strategic Initiatives

Position Overview

We are seeking a dynamic leader passionate about advancing a transformative Jesuit education and creating expanded opportunities for students and the Cristo Rey Jesuit community. As the Director of Strategic Initiatives, you will closely collaborate with senior school leadership to drive mission alignment, strategic execution, and foster collaboration across teams to amplify the institution's impact.

Key Responsibilities

• Act as the main staff contact for the Cristo Rey Jesuit Governance Board, providing comprehensive support to the President on all board-related activities.
• Prepare, coordinate, and follow up on board meetings including agenda setting, scheduling, and documentation to ensure alignment with the school's mission and compliance with bylaws.
• Manage board committees and working groups by organizing meetings, creating materials, tracking actions, and maintaining the online board portal.
• Assist with board member recruitment, orientation, and sustained engagement efforts to strengthen governance.
• Oversee coordination with external strategic planning consultants, serving as a primary internal liaison and project manager for strategic initiatives.
• Facilitate cross-department collaboration among senior leaders to identify opportunities, reduce silos, and monitor progress on key institutional projects.
• Support data gathering, progress tracking, reporting, and evaluation of strategic plans to measure effectiveness and collect stakeholder feedback.
• Design and lead planning sessions, retreats, and meetings to engage senior and broader leadership in strategic efforts.
• Represent the President’s office in cross-functional committees and lead special projects, proactively addressing operational challenges with practical solutions.
• Serve as the institutional liaison for external networks including the Cristo Rey Network, Jesuit Schools Network, and Midwest Jesuits to ensure active engagement and compliance.
• Prepare for and coordinate network site visits, reports, and meetings in collaboration with relevant stakeholders.
• Partner with Human Resources to develop and implement a unified professional development plan that supports staff growth and mission adherence.
• Lead the organization and facilitation of school-wide professional development events with a focus on inclusivity and mission-driven content.
• Cultivate initiatives that enhance organizational culture, fostering a sense of belonging and shared purpose among staff.
• Continuously assess staff needs and gather feedback to refine professional development and culture-building programs.
• Perform other duties as assigned by school leadership.

Qualifications & Skills

• Bachelor’s degree is required; advanced degrees in education, nonprofit management, or related fields are preferred.
• Demonstrated dedication to the Catholic and Jesuit mission of Cristo Rey Jesuit High School.
• Experience navigating complex organizational structures with familiarity in governance, strategic planning, or institutional leadership roles.
• Proven ability to manage multiple projects with strong organizational skills and meticulous attention to detail.
• Excellent communication skills, capable of building trust with board members, staff, and external partners.
• High standards of discretion, judgment, and professional maturity when managing sensitive information.
• Preferred experience includes supporting nonprofit or school governance boards, familiarity with Catholic educational networks, background in organizational development or culture-building, and competence in strategic facilitation and data management.

About Cristo Rey Jesuit High School

Cristo Rey Jesuit Milwaukee is part of a nationwide network of 41 high schools devoted to transforming urban education through a combination of college-preparatory academics, professional experience via a Corporate Work Study Program, and spiritual formation. Serving approximately 450 students primarily from economically challenged backgrounds, the school strives to prepare graduates for success in higher education, careers, and life with affordable Catholic education.

Equal Opportunity

The school is an equal opportunity employer committed to diversity and inclusion, providing access without discrimination based on race, ethnicity, religion, sex, or national origin.