Deputy Chief of Post-Secondary Success

Mastery Charter Schools • Philadelphia, PA

7d • $148,000 - $170,000 • Hybrid

About The Position

The Deputy Chief of Post-secondary Success is responsible for the vision, implementation, and continuous improvement of Mastery’s post-secondary readiness and success strategy. The Deputy Chief leads the postsecondary components of High School Redesign and ensures that students experience a coherent pathway from ninth grade through graduation that prepares them to enter and succeed in college, career training, employment, military service, or another high quality postsecondary option. The Deputy Chief oversees the teams responsible for Mastery’s college and career advising, career-connected learning, durable skills programming, work-based learning, post-secondary partnerships, dual enrollments, high school scheduling, and alumni transition supports. The role works closely with the Academic, Schools, Student Development, Specialized Services, Data, and External Affairs teams to integrate postsecondary readiness throughout the high school experience. The Deputy Chief also manages and develops the central office leaders responsible for post-secondary programming and ensures that they provide high-quality, consistent support to schools.

Requirements

• Deep knowledge of college access, career readiness, workforce development, postsecondary advising, or high school transformation.
• Demonstrated ability to design, implement, and scale complex programming across multiple schools.
• Proven ability to manage and develop leaders, delegate meaningful ownership, establish strong management routines, and address underperformance.
• Strong ability to use data to assess student outcomes, implementation quality, and opportunity gaps.
• Ability to translate strategic goals into clear plans, systems, tools, and expectations.
• Strong change-management, project-management, coaching, facilitation, and stakeholder-engagement skills.
• Ability to drive results through direct management, cross-functional collaboration, and influence-based relationships with school leaders.
• Excellent written and verbal communication skills.
• Unwavering commitment to student success, educational equity, and Mastery Schools’ mission and values.
• Master’s degree in education, counseling, organizational leadership, workforce development, public policy, or a related field required.
• Minimum of 10 years of progressively responsible leadership experience in secondary education, postsecondary access, career readiness, workforce development, or a related field.
• Experience supervising and developing managers or senior leaders.
• Experience leading work across multiple schools, campuses, or organizational units.
• Demonstrated track record of improving measurable student or organizational outcomes.
• Experience working with historically under-resourced students, schools, and communities.
• Ability to physically perform the essential duties of the role as outlined above, and to work in the environmental conditions required, such as traveling to network campuses, monitoring and interacting with students, in-person facilitation of trainings, etc.
• This role may require frequent travel between multiple locations. Reliable transportation is essential to fulfill job responsibilities.

Nice To Haves

• School-based leadership, teaching, counseling, or direct student-support experience is preferred.

Responsibilities

• Develop and communicate a clear, equitable vision for post-secondary preparation and success that aligns with Mastery’s Graduate Profile, Plan 2029, and High School Redesign strategy.
• Design and oversee a coherent ninth- through twelfth-grade progression of academic planning, college and career exploration, advising, work-based learning, application support, and transition planning.
• Translate Mastery’s long-term post-secondary goals into clear annual priorities, implementation plans, milestones, and measurable student outcomes.
• Establish consistent expectations for post-secondary programming across Mastery high schools while allowing schools to adapt implementation to their students and communities.
• Oversee a comprehensive college and career advising model that helps students identify, pursue, and successfully transition into well-matched post-secondary pathways.
• Ensure that students and families receive accurate and timely support with graduation planning, college and career applications, financial aid, scholarships, affordability, enrollment, and transition.
• Oversee the development and expansion of career-connected learning, including career exploration, employer exposure, internships, work-based learning, dual enrollment, and industry-recognized credentials.
• Establish clear quality standards for college advising, career pathways, internships, and other post-secondary experiences, and monitor whether students have equitable access to high-value opportunities.
• Set the vision for partnerships with colleges, employers, workforce organizations, training providers, and community organizations that expand opportunities for students and graduates.
• Establish and monitor a focused set of postsecondary indicators, including ninth-grade on-track status, graduation readiness, FAFSA completion, postsecondary applications, advanced-course participation, work-based learning, credential attainment, postsecondary enrollment, and persistence.
• Use student and implementation data to identify trends, surface opportunity gaps, diagnose challenges, and determine where schools or programs require additional support.
• Lead regular performance reviews with school and central-office leaders and ensure that clear corrective actions are taken when progress is off track.
• Use student, family, alumni, and school feedback to improve programming and determine which initiatives should be strengthened, scaled, redesigned, or discontinued.
• Build the capacity of principals and high school leadership teams to own postsecondary outcomes as a core component of school performance.
• Supervise, coach, and develop the central-office leaders responsible for college access, career-connected learning, postsecondary partnerships, and alumni success.
• Establish clear goals, roles, performance expectations, and management routines for direct reports, and address performance concerns promptly and constructively.
• Ensure that directors and managers provide the majority of direct support to schools, while the Deputy Chief focuses on strategy, talent development, quality assurance, cross-functional coordination, and accountability.
• Partner with the Academic Team to align postsecondary programming with graduation requirements, course pathways, advanced coursework, dual enrollment, academic interventions, and college and career readiness.
• Collaborate with the Schools Team to support principal ownership, school-level implementation, progress monitoring, and differentiated support.
• Work with the Student Development and Specialized Services teams to align advisory, attendance, student supports, and transition planning with postsecondary preparation, including equitable access for students with disabilities.
• Partner with the Data, Technology, Operations, Finance, Human Resources, Legal, and External Affairs teams to ensure that postsecondary initiatives are measurable, sustainable, compliant, appropriately staffed, and well supported.
• Contribute as a senior leader to the ongoing development and refinement of Mastery’s overall high school model.
• Complete other duties and special projects as assigned.
• Represent Mastery in external partnerships, coalitions, conferences, and community forums related to high school redesign, college access, career readiness, and workforce development.

Benefits

• 403(b) retirement plan for PA employees (with a 5% match from Mastery for full-time employees)
• Enrollment in the State of New Jersey Pension Plan for NJ employees
• Robust Employee Assistance Program
• Mental health and counseling programs
• Annual Professional Development Fund
• Discounts and perks at a myriad of retailers, travel organizations, insurance providers, and so much more
• Access to the HealthAdvocate Helpdesk to help you navigate various benefits-related topics.

What This Job Offers

• Job Type: Full-time
• Career Level: Executive