College Transition Specialist

Location: Makawao

Job Posting Title College Transition Specialist Employee Type Regular Recruiting  Start Date
08-03-2026

Job Exempt?

Yes Recruiting End Date
08-26-2026

Aloha mai! Mahalo for your interest in Kamehameha Schools. If you are looking for an opportunity to utilize your skills and talents and grow in your profession, while serving and strengthening our Native Hawaiian community, we would love to have you join our ʻohana!

Kamehameha Schools Maui Campus is seeking a relationship-driven College Transition Specialist who is passionate about supporting alumni as they navigate their post-secondary journeys. The ideal candidate is highly detail-oriented and brings a strong understanding of student development and college readiness, along with experience working with high school or college-aged students. Knowledge of college admissions processes, financial aid systems, event coordination, and FERPA regulations is essential.

This position is ideal for someone who:

Uses data strategically to inform decision-making, evaluate program effectiveness, and identify opportunities for continuous improvement to drive student success initiatives and campus-wide outcomes.

Demonstrates flexibility, creativity, and adaptability when responding to changing student, campus, and community needs.

Builds strong, collaborative relationships with students, families, alumni, colleagues, and external partners.

Communicates effectively and respectfully with diverse audiences while working both independently and as part of a team.

Takes initiative, thinks proactively, and seeks opportunities to strengthen alumni engagement and expand professional networks.

Possesses strong organizational skills and attention to detail, with the ability to manage multiple priorities and programs simultaneously.

A master's degree in Psychology, Communications, Sociology, Business, Higher Education, Counseling, or a related field is highly desirable. Experience supporting college transitions and student success initiatives is strongly preferred.

This is a regular, full-time position with comprehensive benefits.

Job Summary Integral member of the Kamehameha Schools (KS) ʻohana, working with counselors, external partners, students, and their 'ohana to pursue post-secondary opportunities. They will serve as the primary resource for financial aid and transitional programs to empower alumni to continue their education. This role will maintain communication with alumni enrolled in regional colleges to ensure they are supported on their journey to continue their education.

Work both independently and as part of a team that utilizes evidenced based best practice to equip and empower current high school students and alumni with the skills and knowledge, through matriculation workshops, summer and bridge programs, scholarships, life skills, career, and networking opportunities, enrichment opportunities, and other resources, to overcome educational barriers to persist and graduate from college in a timely fashion with minimal debt.

Essential Responsibilities Program Development Build an understanding of campus level educational support services (academic, financial, personal, and career-‐related assistance) for students, allowing them to work in collaboration with staff, faculty, student and/or academic affairs and other key university offices and community agencies, to make necessary referrals, ensuring services are well-coordinated.

Develop and deliver informational programs and workshops targeted towards increasing awareness around post-secondary education enrollment, financial resources, academic, social, and supplemental support services, and career development.

Plans, designs, and delivers new student, parent, and alumni engagement programs, based on shared outcomes to support and align to KS programs, services, projects, and initiatives.

Craft communication for multiple platforms, targeting students, alumni, and 'ohana.

Stakeholder Guidance Manages alumni enrolled in two and four-year colleges, providing advising services focused on college persistence and completion, career readiness, academic and social integration, and transfer options

Serves as a resource for…