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St. Augustine Preparatory Academy

Private K-12 Christian school in Milwaukee

High School Assistant Dean of Student Success

Full-TimePosted on 10/15/2026
$53k - $57k/yr
Mid
Bachelor's, Master's
Milwaukee, WI, USA
In Person
EducationSchool Leadership & Administration

About the job

Requirements
  • The candidate must be mission-driven, demonstrate the highest integrity, and be able to live the values, beliefs, and culture of Aug Prep.
  • The candidate must be bilingual in written and spoken Spanish and English.
  • A bachelor's degree is required, including any other requirements for accreditation.
  • At least two years of teaching or social work experience is required, with a strong record of impacting student achievement and working successfully with students with significant needs.
  • The candidate must be able to work cooperatively and effectively with colleagues and create and nurture a professional community of adult learners.
  • The candidate must demonstrate leadership qualities, seeing the big picture while working directly with students, families, and staff to influence the details driving the overall direction.
  • The candidate must have strong interpersonal and communication skills, including facilitating meetings and presentations and giving and receiving constructive feedback.
  • The candidate must be able to use student-level data to guide instructional decisions.
  • The candidate must have demonstrated teacher leadership with strong pedagogical knowledge and content expertise, or clinical experience with adolescent youth.
  • The candidate must be a participating member of a church.
  • The candidate must demonstrate and possess the highest integrity and be able to live the values and culture of St. Augustine Preparatory School.
Responsibilities
  • Promote positive attitudes, behaviors, and skills that support students’ academic success, attendance, and character development.
  • Encourage and strengthen parental involvement in student achievement and the faith-based school culture.
  • Collect and manage school culture metrics, including attendance, academics, graduation progress, social-emotional well-being, and behavior data.
  • Intervene in and mediate student behavior situations in collaboration with teachers, social workers, advisors, and families; draft behavior plans and document interventions in Infinite Campus as appropriate.
  • Serve as a point of contact for staff and families regarding student behavior, attendance, and culture-related concerns.
  • Promote and maintain strong home-school relationships and support parent engagement initiatives.
  • Oversee systems related to tardiness, absences, and uniforms.
  • Work with parents and students, social workers, advisors, and teachers to resolve situations where policies or protocols have been breached.
  • Report gathered data to the principal, obtain approval for proposed solutions or resolutions, and evaluate the effectiveness of systems and protocols put in place.
  • Act in accordance with federal, state, and local laws, statutes, and policies related to students and families, and consult with school personnel to ensure compliance.
  • Serve as a role model for students by demonstrating professionalism, integrity, and positive behavior.
  • Monitor and support students during morning arrival, lunch, recess, and dismissal.
  • Communicate proactively with students, families, and colleagues.
  • Collaborate with faculty, administrators, and community members.
  • Engage in continuous professional growth through meetings, professional development, coursework, and training.
  • Fulfill assigned school duties, such as supervision or extracurricular involvement.
Desired Qualifications
  • A master's degree is a plus.
  • A state teaching license is preferred but not required.

About the company

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St. Augustine Preparatory Academy

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St. Augustine Preparatory Academy is a private, non-denominational Christian K-12 school in Milwaukee that provides access to private education primarily through state voucher programs for students from minority and low-income backgrounds. It operates a four-pillar model—faith, family, academics, and athletics/arts—with personalized instruction and specialized classrooms, supported by modern technology and substantial facilities. It differentiates itself through its large, campus-scale approach (the largest single-campus K4-12 in Wisconsin plus an upcoming second campus), explicit Christian ethos for teachers, and strong performance metrics such as a five-star DPI rating. Its goal is to close the educational achievement gap by expanding access, capacity, and leadership development for underrepresented communities through continued philanthropic support and multi-campus growth.

Company Size

51-200

Company Stage

N/A

Total Funding

N/A

Headquarters

Milwaukee, Wisconsin

Founded

2017

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Simplify's Take

What believers are saying

  • North Campus raised over $22 million by January 2026, signaling strong donor momentum.
  • Aug Prep expects about 2,700 students across both campuses in 2026-27.
  • Fall 2026 North Campus opening adds 330 students and expands Milwaukee neighborhood reach.

What critics are saying

  • Wisconsin lawmakers proposed 2026-27 voucher caps; Aug Prep depends on that stream.
  • North Campus opening slipped from 2025 to August 2026 after site condition reviews.
  • Student walkout tensions in January 2026 exposed discipline friction around immigrant-rights activism.

What makes St. Augustine Preparatory Academy unique

  • Gus Ramirez’s family funded a $100 million two-campus buildout since 2017.
  • Aug Prep earned top-5% statewide growth and consecutive Wisconsin DPI exceeds-expectations ratings.
  • Christian K4-12 model combines voucher access, elite facilities, and explicit faith formation.

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Benefits

  • Health Insurance
  • Dental Insurance
  • Vision Insurance
  • Disability Insurance
  • 401(k) Company Match
  • Professional Development Budget