Director of Middle School Programs

The Academy Group, Inc.•Chicago, IL

2d•$98,500 - $115,500•Onsite

About The Position

The Academy Group (AG) is a unique social enterprise that leverages earned revenue from financial investments to create world-class opportunities for young people from the nation’s most resilient communities. The Academy Group demonstrates the promise of a new model for identifying, developing, and sustaining a diverse national pipeline of future leaders, employers, and change agents. We were founded based on a unique model. One that creates pathways for young people from resilient communities who demonstrate relentless perseverance to build wealth and become socially just change agents, ideally through careers and leadership positions in our portfolio companies. No other organization in the world is built to do this. The Role The Director of Middle School Programs is a senior, mission-critical leader within The Academy Group. The Director is responsible for the design, management, execution, and continuous improvement of the Academy’s middle school model, serving members in grades 7–8 and laying the foundation for long-term academic success, strong high school transitions, and future college and career readiness. The Director ensures that every middle school member experiences exceptional academic, social-emotional, and developmental support, while also building the agency, confidence, and habits necessary to excel in school, work, and life.

Requirements

A Master’s Degree or higher is preferred in educational administration, MBA, or a related field
Minimum of 7 years of teaching, school counseling, or related experience
Minimum of 5 years of program management and adult supervision experience
Successful experience serving young people from resilient communities
Experience working in a fast-paced and innovative environment
Understanding of current trends and best practices in education and adolescent development.
Strong written and verbal communication skills; a persuasive and passionate communicator with excellent interpersonal and multidisciplinary project skills
Ability to work effectively in collaboration with diverse groups of people
Passion, idealism, integrity, positive attitude, mission focus, and autonomous nature
Knowledge of current community challenges and opportunities relating to the mission of the organization
Ability to work under dynamic, evolving conditions

Responsibilities

Oversee the vision, scope, and structure of the middle school program (grades 7–8), aligned to the Academy’s broader 14-year journey
Designs and continuously refines the middle school advising model, curriculum, milestones, and outcomes
Ensures alignment between middle school programming and high school readiness goals
Uses data, research, and student outcomes to iterate on program design and delivery
Leads cross-functional planning with data, high school, career, and family engagement teams
Oversees the delivery of individualized, small-group, and cohort-based supports for middle school students
Ensures consistent, high-quality advising experiences across all middle school cohorts
Sets expectations for member caseload structures, advising cadence, and intervention protocols.
Builds strong relationships with families to support academic success and key transitions.
Manages the Summer Pathway program and engagement with families and strategic vendors.
Oversee the private school scholarship fund and work closely with families and private high schools’ administration teams.
Directly supervises middle school advisors and/or program staff.
Sets clear performance expectations aligned to program goals and Academy values.
Coaches, develops, and evaluates staff through regular observations, feedback, and professional development.
Builds staff capacity in adolescent development, advising practice, member-centered approaches, and data-informed decision-making.
Manages day-to-day program operations, ensuring strong execution and follow-through.
Oversees program calendars, advising structures, member milestones, and family engagement touchpoints.
Ensures systems for documentation, data tracking, and progress monitoring are consistently used.
Identifies risks, gaps, and opportunities early and implements corrective actions.
Partners with operations and finance teams to manage program budgets and resources.
Monitors academic, attendance, and qualitative program data.
Ensures the middle school program meets defined outcomes related to readiness, engagement, and persistence.
Serves as a thought partner to senior leadership on middle school strategy and growth
Represents the middle school program internally and externally
Contributes to organizational planning, cross-team learning, and culture-building
Models the Academy’s values and expectations in all interactions