Are you called to use your leadership, strategic thinking, and collaborative spirit to advance a transformative Jesuit education and expand opportunities for students and for the School?
If yes, this is an opportunity to make a lasting impact. As the
Director of Strategic Initiatives, you will partner with school leadership to advance the mission, align strategy with action, and bring people and ideas together to create meaningful opportunities for students and the Cristo Rey Jesuit community.
Job Summary
The
Director of Strategic Initiatives serves as a senior strategic partner to the President and School Leadership Team, advancing the mission of Cristo Rey Jesuit High School by facilitating governance excellence, leading strategic planning processes, strengthening relationships with key organizational partners, and cultivating a vibrant professional culture. Assisting the President, this role provides executive-level representation across cross-functional initiatives, drives institutional alignment, and moves high-priority special projects forward with clarity and accountability. This role is designed for a mission-driven leader who moves fluidly between high-level strategy and hands-on facilitation, bringing people, data, and ideas together to drive institutional impact.
Responsibilities
Governance Board Support
- Serve as a primary staff liaison to the Cristo Rey Jesuit Governance Board, supporting the President in all board-related matters
- Ensure productive, mission-aligned board meetings through agenda development, pre-meeting preparation, and post-meeting follow-up
- Provide dedicated support to board committees, subcommittees, and working groups - including scheduling, materials preparation, minutes, and action tracking
- Maintain the board's online portal, ensure bylaw compliance, and record governance changes with accuracy and care
- Assist the President with board recruitment, orientation, and ongoing engagement
Strategic Initiatives
- Coordinate with the school's external strategic planning consultant, serving as a key internal point of contact and project manager
- Facilitate cross-departmental conversations to surface opportunities for collaboration and alignment across school functions, working closely with senior leaders to break down departmental silos and track progress on institutional initiatives
- Support data collection, tracking, and reporting related to strategic plan metrics; conduct post-project evaluations to assess institutional impact and program effectiveness, gather stakeholder feedback, and document best practices
- Design and facilitate strategic planning sessions, retreats, and working meetings with senior and extended leadership
- Represent the Office of the President on internal cross-functional committees and working groups to ensure alignment; lead and advance special projects assigned by the President; proactively identify operational bottlenecks, resource constraints, or timeline risks, propose solutions, and assist with solution implementation.
Network & Accrediting Body Relations
- Serve as a key institutional liaison to the Cristo Rey Network, Jesuit Schools Network, and Midwest Jesuits, supporting CRJ's active participation in and compliance with each organization
- Coordinate and prepare materials for site visits, reporting requirements, and network convenings in partnership with the President and relevant staff
- Track deliverables, deadlines, and commitments across network relationships, ensuring CRJ meets its obligations with excellence
Professional Development & Organizational Culture
- Partner closely with Human Resources to design and implement a cohesive professional development strategy that supports staff growth and mission alignment
- Lead planning and facilitation of school-wide professional development days and related programming, ensuring content is mission-aligned, purposeful, inclusive, and impactful
- Develop and steward ongoing culture initiatives that deepen belonging, connection, and shared mission across CRJ's staff community
- Assess staff needs and gather feedback to continuously improve PD and culture offerings
- Other duties as assigned
Required
QUALIFICATIONS AND SKILLS:
- Bachelor's degree required
- Demonstrates commitment to the Catholic and Jesuit mission of Cristo Rey Jesuit High School
- Experience in a complex organizational environment, with exposure to governance, strategic planning, or institutional leadership
- Strong project management and organizational skills, with a track record of managing multiple priorities with follow-through and attention to detail
- Outstanding written and interpersonal communication skills; able to build trust with board members, staff, and external partners
- High degree of discretion, judgment, and professional maturity when handling sensitive or confidential information
Preferred
- Bachelor's degree or advanced degree in education, nonprofit management, organizational development, or a related field preferred
- Experience supporting nonprofit or school governance boards
- Familiarity with the Cristo Rey Network, Jesuit Schools Network, or Catholic school ecosystems
- Background in organizational development, culture-building, or professional learning design
- Experience with strategic planning processes, including facilitation and data management
About Cristo Rey Jesuit High School
Cristo Rey Jesuit (CRJ) Milwaukee is part of a national network of 41 high schools that transform urban education through a unique integration of college-prep academics, professional experience, and spiritual formation, with a focus on students of limited financial means. As a private, Catholic, Jesuit high school serving 450 students, Cristo Rey Jesuit's mission is to provide an affordable Catholic secondary education with a college-prep curriculum and a Corporate Work Study Program to prepare graduates for success in college, work, and life.
Interested
For more information or to apply, please visit our website directly by using this link: https://cristoreymilwaukee.isolvedhire.com/jobs/
We kindly ask that you do not email your resume, as all applications are accepted through our Join Our Team page only.
Direct questions to gbushman@cristoreymilwaukee.org
Cristo Rey Jesuit High School Milwaukee is an equal opportunity employer that provides equal employment opportunities to applicants without regard to race, ethnicity, religion, sex, or national origin.
