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 tools.

• Use data to identify trends, gaps, and opportunities to strengthen alumni support systems.

• Contribute to alumni communications, newsletters, and other program materials as needed.

• Participate in cross-team planning, reflection, and internal meetings that strengthen the overall Graduate Success Program.

Qualifications and Requirements

• Bachelor’s Degree required; Master’s Degree in Education, Counseling, Social Work, or related field strongly preferred.

• Minimum of 3-5 years of related work experience in alumni support, college counseling, or educational leadership.

• Fluency in oral and written Spanish.

• Experience working with BIPOC, first-generation, or immigrant students and families.

• Demonstrated ability to build partnerships and coordinate supports that advance student persistence and postsecondary success.

• Strong personal commitment to our school values; a growth mindset, curiosity, and humility.

• Advanced knowledge of student success strategies, outreach initiatives, and financial literacy (FAFSA, loans, scholarship support) for underrepresented students.

• Exceptional organizational and time management abilities, with a focus on program design and execution.

• Ability to design, implement, and evaluate programs that address the needs of diverse student populations, using both qualitative and quantitative data.

• Availability for limited evening or weekend events, and flexibility to travel to schools and colleges across New England as needed.

• Ability to drive to campus visits, requiring a valid U.S. driver’s license.

Compensation

Salary range: $70,000-$80,000 annually.

Esperanza Academy offers an attractive benefits package including 403(b), medical, dental, life, and disability insurance, and a comprehensive professional development program.

To Apply

Please send a cover letter specifically detailing your qualifications for the position, a resume, and contact information for three professional references to Jadi Taveras, Head of School, at employment@esperanzaacademy.org

Esperanza will only accept applications from individuals currently authorized to work in the U.S.

Non-Discrimination Policy

Esperanza is committed to a diverse and inclusive community with respect to race, national origin, religion, gender, sexual orientation, family status, economic circumstance, age, and physical disability in its student body, faculty and staff. Esperanza Academy does not discriminate on the basis of race, color, national and ethnic origin in the administration of its educational policies, admission policies, and athletic and other school-administered programs. Esperanza Academy is an Equal Opportunity Employer.