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Director of Advisory 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. We expect to establish Academies in cities across the nation in the years ahead.  Academy 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 Director of Advisory is responsible for overseeing vision, design, development, and execution of advisory framework, pedagogy, and structure. Through direct oversight, counseling and coaching of advisors, The Director of Advisory will, by extension, advise all elementary, middle, high school and college students in the Chicago Academy. In this capacity, the director will balance creative and sustainable measures to maximize our assistance to all students and advisors.

In addition to the responsibilities regarding advising, the director will work closely with other Directors and senior team members to enhance all operations. Specifically, the director will team with the Director of College Attainment on transition efforts to ensure sustainable support and mentorship for The Academy Group college students.

As we launch the Chicago Academy, the director will work with senior staff to recruit, vet, and hire all advisors. In order to maintain exceptional quality, and ensure students are supported to meet The Academy Group’s goals, the director will institute and direct processes for on boarding, training and evaluating advisors, and work with senior leadership to assess and adjust the program over time.

Success will require the director to have a deep knowledge of advising systems and student development; leadership aptitude and ability to harness the assets of diverse teammates; consciousness of social justice and systemic inequity; willingness to create and modify programming based on evidence, new ideas, and individual student needs; incorporating empathy and trauma informed interventions within programs and structures; and being authentic. In addition, a critical measure of success for the director will be the ability to design an advising framework built on the tenets of agency (as defined by authentic student voice, choice, and ownership) and belief (as defined by student trust and confidence in their skills, abilities, and value.

The Director’s approach to work should reflect the core values and habits of the Academy staff: tireless focus on excellence, determination in spite of obstacles, impeccable integrity, willingness to work hard, ability to learn from multiple sources, relentless focus on results, constant reflection and self-awareness, zest, social intelligence, and pertinacity.

The director role is a Chicago Academy position, with room to evolve into a national Academy Group role.  In the near term, the Director of Advisory will report to the Chief Learning & Design Officer.


  • Design systems of advising, mentorship, and additional support
    • Architect advising strategy for fourth-grade through college with key goals and adjustments to levers of support depending on evidence of effectiveness and individual student needs
    • Create peer support strategy—balancing innovative approaches and reasonable student involvement to achieve stronger organizational-wide support and inter- and intra-grade level support
  • Develop staff competency and skills
    • Recruit, hire, and provide ongoing support and supervision for advisors
    • Provide ongoing support and supervision for advisors, identifying clear skills and competency needs across the team
    • Develop vision to elevate advising staff skills and expertise and keep current on evidence based advising and mentoring practices
    • Instill a culture of data-driven, intensive individualized support, rapid response to issues as they arise, and tracking and responding to all aspects of student growth and development
    • Employ a mindset of asset-based thinking among staff
  • Develop organizational culture
    • Establish a culture of academic excellence by working with site leadership to develop rituals and activities to build organization’s identity
    • Embody The Academy Group’s core values at every turn
  • Collaborate with the Director of College Attainment on college transition
    • Team with Director of College Attainment to identify advising, mentorship, and additional supports for students attaining degrees across the nation and globe
    • Establish strong connections between advising with college counseling efforts—with a special focus on junior and senior year of high school
  • Manage day to day advising program (Start-up role)
    • Oversee all aspects of the operations of advising (design, development, execution etc.)
    • Assist with other programs as requested by leadership

Shared Responsibilities

  • Foster a culture of academic excellence
  • Collaborate and implement support planning and policies
  • Promote individual student success
  • Communicate with parents/guardians regarding student progress
  • Coordinate departmental and other student advising meetings
  • Collaborate with team to identify potential partners for student supports, including social emotions, college preparation/transition, and other types of support

Who we are looking for

Qualifications and Experience

  • Bachelor’s degree; Master’s in education or related field preferred
  • Minimum of 5 years advising or education experience including:
    • Two years classroom experience
    • Three years administrative or education advising program leadership experience focusing on students of color, lower socio-economic students, and 1st generation college-bound students
  • Background in counseling, psychology, mental health, social emotional learning, human development, and/or neuroscience


  • Experience in the supervision of staff and an ability to evaluate the effectiveness of advising
  • Proficiency in mentorship models
  • 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
  • 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, integrity, zest, 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

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