The Academy Group, Inc. · 1 day ago
Director of Middle School Programs
Chicago, IL, US
Full-time
Onsite
Director/Executive
$98K/yr - $116K/yr
7+ years expThe Academy Group, Inc. is a unique social enterprise focused on creating opportunities for young people from resilient communities. The Director of Middle School Programs is responsible for designing and managing the middle school model, ensuring that students receive exceptional academic and developmental support while preparing for high school and future careers.
CommunitiesSocialTutoring
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
Qualification
Required
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
Benefits
Comprehensive medical, vision, dental, and 401 (k) package
Company
The Academy Group, Inc.
Through rigorous, hands-on exploration of economics, entrepreneurship, design thinking, and justice, the Academy Group helps young people acquire the skills and mindsets to lead, own and create opportunities for their families and communities.
11-50 employees
Funding
Current Stage
Early StageLeadership Team
Ted Christians
Chief Executive Officer, Amplify Chicago
Shayne Evans
Managing Partner
Company data provided by crunchbase