Job Description

Associate Director of the Academy Chicago

Who We Are

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 is demonstrating 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 upon a unique model. One that creates pathways for black and brown students, if they demonstrate relentless pertinacity, 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 Associate Director (AD) at the Academy Chicago works in close partnership with the Executive Director to build an organizational strategy and program model that are aligned to the organization’s mission statement; and differentiated to meet the needs of students and school partners. The AD is responsible for designing and facilitating a leadership coaching plan that supports the development of the Chicago Team. This development will result in the identified personnel meeting their individual, team, and organizational goals. In addition, the AD is responsible for building local data analysis cycles and managing the submission and reporting of information specific to students’ performance. Also, the AD collaborates with the Executive Director to plan, deliver, and monitor student programming (Summer and School-Year). Additional duties include but are not limited to student and family communications, staffing, management of Academy Chicago Google Drive, and performance evaluations.

Principle Duties and Responsibilities

Organizational Leadership, Strategy & Program Design:

  • Collaborate on the design of the Academy Chicago strategy and program model
  • Design phase-out & phase-in model for the external intervention and enrichment program
  • Coordinate the design and delivery of the school-based advisory program
  • Design role charters for Academy Chicago team members and facilitate one-to-one meetings (align role charter to new program model)
  • Design, manage, & facilitate programmatic & school-based data cycles
  • Build professional development session that ensures transparency across organizational roles
  • Oversee academic programming including development, implementation and execution of
    academic schedules, ensure seamless integration of internal program and external providers
  • Develop strategy to onboard summer and school year program staff and facilitate collaborative planning among summer teaching staff. Ensure teachers deliver a world class academic program incorporating innovative, rigorous, and engaging daily lesson plans
  • Oversee day to day operations of the Academy Group including areas of facilities, transportation, safety and security, student services, stakeholder communication, and program coherence.
  • Ensure all compliance (fiscal, academic, safety, local/state/federal) guidelines are satisfied across all programming locations and field journeys.
  • Collaborate with a team to develop and implement year round programming and support.

Leadership Development & Coaching Model:

  • Develop coaching plans for team leaders
  • Develop team members’ knowledge, skills, attitudes, and behaviors through a variety of professional development targeted topics and designs
  • Provide strategic support to individual staff members and collaborative teams. Track leadership development through coaching logs and other artifacts

Manage Program Operations:

  • Support elementary school-day academic programming including visiting school sites,
    supporting Director or team leader weekly team check-ins
  • Organize and manage summer and school-year program launch punch lists
  • Organize, share, and manage annual events calendar
  • Manage the Academy Chicago Google Drive folders

Family and Stakeholder Engagement:

  • Facilitate school partner meetings
  • Support with the annual parent orientation sessions
  • Support with the high school and college awareness parent engagement sessions
  • Support with the distribution of annual student stipends

Professional Responsibilities & Other:

  • Foster an adult culture of professional and operational excellence
  • Foster a culture of adult collaboration and professional development
  • Promote individual student success
  • Ensure all compliance (fiscal, academic, safety, local/state/federal) guidelines are satisfied)
  • Collaborate with Executive Director and team leaders on the program model design and
    delivery of Summer Academy and school-year programming
  • Ensure consistent data collection to monitor the impact of student programming

Additional Shared Accountabilities/ Duties

Qualifications and Experience

  • Bachelor’s degree; Masters in education or related field preferred
  • Minimum of 7 years academic experience including:
    • 3+ Classroom experience; preferred candidates have experience working across multiple grade levels
    • 2+ years leadership experience focusing on instructional design, development and/or supervision and coaching

Demonstrated Attributes

  • Demonstrated evidence of relentless pertinacity in both their professional and personal background
  • Knowledge of current community challenges and opportunities relating to the mission of the organization
  • Strong written and verbal communication skills; a persuasive and passionate communicator with excellent interpersonal and multi-disciplinary project management skills
  • Ability to work effectively in collaboration with diverse groups of people, specifically students from the “most resilient communities”
  • Demonstrated analytical skills; must be highly efficient with a strong attention to detail
  • Passion, integrity, zeal, mission-focus, and disciplined work ethic


This position will be based in Chicago, IL.

Compensation and Benefits

The Academy Group offers a competitive salary and comprehensive medical, vision, dental and 401k package.

How to Apply

Please send your resume and a short (<250 words) note about your interest in the role to