Assistant Director at the Chicago Academy

Job Description

Who We Are

The Academy Group (AG) is a unique enterprise founded to realize the long-term potential of young people from underserved communities across the United States.  Designed to tap into the deep wells of often overlooked talent that exists nationwide, the Academy Group empowers youth to thrive in school, work and life.

In 2017, we launched the Chicago Academy, with an enrollment to grow to 1000 students. We expect to establish Academies in cities across the nation in the years ahead.  Academy Group students develop the agency and belief to excel. They receive high dosage, individualized academic programming from elementary school through college; a case-based business curriculum focused on building entrepreneurial, financial and analytic expertise; college and career counseling; rigorous job preparation and internships and; personalized advising and executive mentoring. Students attend their home schools, colleges and universities – with Academy programming occurring after school, on weekends and throughout the summer.  The core values of the Academy Group are Excellence, Determination and Justice.

The Academy Group is built on a sustainable business model that aligns the commercial and social sectors.  The Academy Group take ownership stakes in a diverse portfolio of commercial companies. The earned revenue generated from the Academy Group companies funds the education programs, provide apprenticeships for students through college, and create employment opportunities to Academy Group graduates. 

Ultimately, the Academy Group aims to generate a new class of innovators and leaders by delivering long-term opportunities for exceptional young people to own, operate and create successful companies across multiple sectors.  


The Assistant Director (AD) at the Chicago Academy works in close partnership with leadership at the Chicago Academy to establish and maintain program culture and execute day to day operations in support programs delivered across the city.  The AD is responsible for working with teaching staff to develop, execute, and implement the Academy Group’s culture management policy and in doing so work with students to embody our core values (Excellence, Determination and Justice) in all of their pursuits as AG students.  The AG will also be charged with designing and implementing programming designed to foster and build community across student groups. In addition to maintaining culture, the AD supports all day to day operations of the Chicago Academy. Duties include but are not limited to student scheduling, facility and transportation management, and student and family communications.  

Additionally, the AD collaborates with the Executive Director and Director of Academics of the Chicago Academy to hire and manage all student facing academic staff including full time and part time teachers and tutors. The AD will work in concert with peers to maintain academic quality of programming providing assisting in providing oversight and developmental support for teaching staff in order to achieve the Academy Group’s target goals.

In this capacity, the AD will work closely with the national and regional team to head all academic and operational functions in support of the Summer Academy.  As the Academy Group grows, the AD will hold significant responsibility for managing and executing expanding programming offerings.

Success in this role will require multifaceted expertise in operational management and execution and curricular design.  Candidates should possess the vision and ability to successfully implement processes that develop and execute rigorous, “break the mold” coursework. The AD must have deep experience working in and building exceptional academic institutions that achieve persuasive results, maintain the highest standards of excellence and professionalism, use data to evaluate outcomes and make necessary programmatic changes.  Candidates must also have a demonstrated ability to work closely with partners and the Academy staff, to construct and refine high quality academic programs that improve outcomes for youth.

The Assistant Director reports to the Executive Director (ED) of the Chicago Academy.


  • Manage program operations
    • Support academic programming including development, implementation, and execution of academic schedules, ensure seamless integration of internal program and external providers
    • Develop strategy to onboard summer staff and facilitate collaborative planning among summer teaching staff
    • Ensure teachers are delivering a world class academic program incorporating innovative, rigorous, and fun daily lesson plans
    • Oversee day to day operations of the Chicago Academy including areas of facilities, transportation, safety and security, student services, stakeholder communication, and program coherence
    • Collaborate with team to develop and implement year round programming and supports
  • Lead culture and community building 
    • Implement and refine student culture engagement policies that support the pursuit of the Academy Group’s core values and objectives
    • Build and execute programming to internalize our core values and build community.  Programming includes new student orientation, daily assemblies and student celebrations
  • Foster instructional excellence
    • Work with Academic team to oversee teaching staff in developing rigorous curricula in support of the Academy Group’s vision and objectives
    • Support the ED and Academic team as an instructional coach ensuring high quality delivery of academic content from all student facing academic staff including teachers and tutors

Additional shared accountabilities/duties

  • Foster a culture of academic and operational excellence
  • Promote individual student success
  • Communicate with parents and partners regarding student academic progress and program updates
  • Ensure all compliance (fiscal, academic, safety, local/state/federal) guidelines are satisfied.
  • Collaborate with leadership to finalize design of the Summer Academy, including program calendar, daily schedule, and daily operational plan
  • Ensure consistent data collection to monitor impact of programming

Who we are looking for

Qualifications and Experience

  • Bachelors degree; Masters in education or related field preferred
  • Minimum of 5 years advising or education experience including:
    • A minimum of three  years of classroom experience; preferred candidates have experience working across multiple grade levels
    • A minimum of two years of leadership experience focusing on instructional design, development and/or supervision and coaching
  • Ability to drive exceptional academic results for students
  • Experience in the supervision of faculty members and an ability to evaluate the effectiveness of program instruction
  • Ability to design and implement core academic programming
  • Excellence in organizational management with the ability to coach staff, manage, and develop high-performance teams, set and achieve strategic objectives, and manage a budget


  • Excellent time management, organizational skills and flexibility working in a fast paced and constantly evolving start-up environment
  • Self-starter who can manage workload effectively with competing demands for time, comfortable working autonomously
  • Commitment to serving people, organizational development, creating processes that better serve our team
  • Highly adaptable, resourceful, ability to think creatively and approach things differently
  • Strong written and verbal communication skills; a compelling communicator with excellent interpersonal and multidisciplinary project skills
  • Ability to work effectively in collaboration with diverse groups of people
  • Passion, integrity, zest, mission-focus, and autonomous nature
  • Knowledge of current community challenges and opportunities relating to the mission of the organization
  • Ability to maintain a high level of confidentiality

This position will be based in Chicago.

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

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