Associate Director of Graduate Success, Student Success & Postsecondary Support (at Esperanza A[

Associate Director of Graduate Success, Student Success & Postsecondary Support

Esperanza Academy, an independent middle school for girls in Lawrence, Massachusetts, seeks a relational, organized, and mission-driven Associate Director of Graduate Success, Student Success & Postsecondary Support. This role provides direct support to students, graduates, and families across the high school and early postsecondary years, helping them navigate academic transitions, financial aid, college decision-making, persistence, and early career planning with the goal of empowering them to achieve success.

The Associate Director works closely with the Chief Alumni Success Officer and the Graduate Success Program team to support key elements of high school preparation and transition work while maintaining a primary focus on advising and caseload support for students in grades 9-12 and the early postsecondary years. This role is especially important in helping students and families make informed financial decisions, access resources, and remain connected to Esperanza’s long-term network of support.

This is an ideal role for someone with strong advising instincts, experience guiding students and families through financial aid and postsecondary planning, and a deep belief in relationship-based support for first-generation students and families.

About Esperanza: For more than two decades, Esperanza has paired rigorous academics with a long-term commitment to its students, supporting them through middle school, high school placement, college navigation, and early career development. As the school moves into its new home and expands its reach, Esperanza is positioned not only to serve more students and families, but also to contribute to national conversations about what equitable, justice-centered education can look like.

KEY RESPONSIBILITIES

Student, Graduate, and Family Advising

• Manage a caseload of Esperanza graduates in high school and the early postsecondary years, offering academic, social-emotional, financial, and advising that supports long-term success and stability.
• Build strong relationships with students, graduates, and families through regular communication, one-on-one meetings, office hours, events, and individualized support.
• Guide students and families through key financial aid and college affordability decisions, including FAFSA completion, award letter review, appeals, scholarship applications, student loans, and persistence-related financial planning.
• Support students and graduates with postsecondary transitions, college persistence, career exploration, resume development, and workforce readiness.
• Coordinate outreach and intervention for students or graduates experiencing academic, financial, or personal challenges.

High School Preparation and Transition Support

• Contribute to admissions-related support for middle school students and families, especially around transition into high school and understanding school fit, opportunity, and affordability.
• Co-facilitate and support selected high school preparation classes, workshops, and family-facing programming for 7th- and 8th-grade students.
• Help ensure the continuity of Esperanza’s support across all stages, middle school, high school, and postsecondary.

Postsecondary Programming and Partnerships

• Partner with the Chief Alumni Success Officer and peer Associate Director to coordinate postsecondary and alumni programming, including workshops, events, and resource-sharing related to college persistence, financial literacy, and workforce development.
• Cultivate and sustain partnerships that expand opportunity for students and graduates, especially in financial aid, college access, career exploration, and economic mobility.
• Help strengthen alumni connection and engagement through outreach, relationship-building, and coordinated opportunities to remain connected to GSP.
• Use student and alumni data, documentation, and program insight to help strengthen interventions and improve support over time.

Systems, Documentation, and Program Support

• Maintain clear systems for caseload management: track alumni academic, career, and financial milestones in Salesforce and other tracking…