Employment Opportunities

Bennett Day School’s goal is to build a top-tier independent school with passionate and highly-dedicated team members that strive for excellence. Our current openings are listed below. Please review and select any positions in which you are interested in applying for to be directed to the online application process. If you have any questions, email us at personnel@bennettday.org

Full-Time Positions:

Director of Sales and Marketing

Bennett Day School Director of Sales and Marketing


Bennett Day School, Inc., a rapidly growing private preK-12 school delivering world-class dynamic project-based learning (PBL) in the West Loop in Chicago, is seeking a Director of Sales & Marketing. 


Reporting directly to the CEO, this new position is responsible for: (1) marketing to generate new leads and (2) sales to convert leads to enrollments. Experience creatively building B2C services brands, engaging with local communities, and leveraging media and PR coverage is key for our marketing efforts. Exceptional candidates will have a background as a high-energy, hungry salesperson who consistently exceeds their performance targets and has deep experience bringing out the best in those they manage too. The Director will train, mentor, grow, and hold accountable our existing marketing and enrollment sales teams in order to optimize every point of the marketing and sales cycle from marketing qualified lead, to sales qualified lead, to application, to enrollment. Excellent candidates will exemplify the core competencies of our Bennett BADGE: Big-Picture Thinker; Adept Problem Solver; Data-Informed; Great Team Player; and Effective Communicator. 


  • Train, mentor, grow, and hold accountable marketing and sales teams.  
  • Establish a high-energy, eager sales culture that motivates and incentivizes outperformance.
  • Manage the enrollment sales team and optimize the application processes for new students. 
  • Analyze measurables by creating and monitoring reports and CRM data; employ intellectual curiosity to always improve and grow, always increasing the focus on data. 
  • Drive business development by executing strategies to maximize marketing / sales potential.
  • Drive the ROI on the entire marketing and sales cycle; be proactive, think ahead of the CEO.
  • Manage compelling, distinctive brand messaging while leveraging psychographics / personas.
  • Manage marketing and sales budget. 


  • Oversee and manage the enrollment team and processes to exceed all enrollment targets. Employ strategy for continuous improvement at every point in the marketing and sales cycle. 
  • Actively, consistently monitor team scorecard and other KPIs to maintain traction. Leverage reports that drive and incentivize desired behaviors. Make daily decisions based on data. 
  • Create an employer outreach program. Identify optimal targets and build relationships.  Leverage our lab school relationship with Northwestern University. 
  • Execute a robust calendar of community events to reach families in target neighborhoods; create weekly opportunities for school community members to be Bennett ambassadors.
  • Support the team to methodically nurture relationships with feeder programs and schools.
  • Develop channel strategies and staffing plans to assure optimal business development.
  • Maximize nurturing campaigns; continue to advance digital demand; optimize spend. 
  • Create persona and content strategies across all social media platforms to drive efforts. 


  • We are looking for what you’ve achieved and how you’ll apply it vs. the # of years you did “x”.
  • Deep sales & marketing experience; a background of consistently outperforming sales targets.
  • Management background required in leading, training, mentoring, and growing collaborative sales and marketing teams while building meaningful internal and external relationships.
  • An MBA or bachelor’s degree in sales, marketing, business management, or related fields.
  • Successful history of both creating and converting opportunities in B2C services is preferred.
  • Experience using and optimizing HubSpot or similar CRM systems is required.
  • Understanding of multi-channel, digital, psychographic, and traditional marketing is preferred.
  • Excellent candidates will exemplify Bennett BADGE core competencies: Big-Picture Thinker; Adept Problem Solver; Data-Informed; Great Team Player; and Effective Communicator. 


  • Base pay and incentive compensation. 
  • Health, dental, and vision benefits.
  • STD, LTD, Life, Transit, HSA, FSA
  • 401(k) with matching.
  • Tuition benefit for children to attend Bennett Day School.

About Us:  

At Bennett Day School in our PreK to 12th grade private school campus in the West Loop in Chicago:

(1) We deliver dynamic project-based learning (PBL) experiences and resources for children and adults that empower us to live and lead purposeful lives. We learn by doing.

(2)  Students and teachers co-construct learning. We are learner-centered; learning is personalized.

(3) Competency-Based Education (CBE) is documented in a digital portfolio and format valued increasingly by colleges and universities. We focus on learning outcomes that are purposeful.

Opened in 2014 with just 23 students, Bennett now has 300 students in PreK through high school. We begin construction on a new wing in 2022 to enable us to more than double enrollment to over 600. Bennett was recognized nationally in the 2020-2021 school year as an exemplary school by the U.S. Department of Education for its reopening strategies during the pandemic to provide in-person school to all students at all grades every day of the entire school year when it was possible to do so. 

Nominated for the Chicago Innovation Awards, Bennett is a lab school partner to Northwestern University and collaborates closely on classroom and research projects with the faculty in the School of Education and Social Policy to give our students and teachers experiences alongside NU faculty. University employees also receive a tuition benefit for their children to attend Bennett. A member of Conscious Capitalism, Bennett Day is a tax-paying social enterprise backed by the Code Family Foundation, Wintrust, Chicago ArchAngels, and numerous others with a passion to shape school as it was once meant to be, and now needs to become, to prepare our children for the next century.

JOB TITLE: Director of Sales & Marketing 

FLSA STATUS: Exempt, Salaried


If interested, please apply HERE!

Bennett Day School is an equal opportunity employer.

Director of Intermediate and Middle School

Bennett Day School  Intermediate and Middle School Director 

Bennett Day School is a progressive independent day school looking for passionate educators with an innovative spirit and rich background in learning and school experience.  We are a new type of independent school; unabashed believers in the values of progressive education, we put students at the center of the process of learning.

Bennett Day School is hiring an Intermediate and Middle School Director. In this role, you’ll be part of the educational team and be responsible for implementing the core characteristics of our progressive, project- and competency-based intermediate and middle school.


The Intermediate and Middle School Director position will evolve over the next two years. We have grown significantly over the past eight years, and are currently transitioning from a start-up school to a more established institution. The Bennett Day Middle School, currently only grade 6, opened 2020-2021. The Middle and Intermediate School is at the epicenter of that transition; our 5-7th grade classes contain many “founding” families who have been with the school since its inception. We have a high school that began two years ago, so the intermediate and middle school role will exist between the oldest and newest divisions within the school. 

The position will encompass grades 2-7. You will take on the role of Director of Intermediate and Middle School, grades 3-8, in 2022-23. Reporting to our principal, you’ll bring your experience to the team to oversee and manage the intermediate and middle years program that is true to our progressive mission. 

As one of our Division Directors, you’ll be intimately involved in every aspect of the educational program of our school, and have input into major pedagogical and/or curricular decisions that the school makes. You’ll interact with parents, faculty and students on a daily basis, and you’ll bring your management experience with you each day to engage in the oversight of the day-to-day program. You’ll have the opportunity to develop meaningful educational relationships with other administrators, including our education and executive team, as well as our intermediate and middle school faculty. You’ll also learn from your colleagues during weekly education team meetings, as well as the 5+ hours per week of professional development, which occur on Wednesdays when students are released early. 


  • 5+ years experience working with children and/or adolescents in an education setting
  • Experience in a school that uses an interdisciplinary or team-teaching approach
  • Interest in/Experience working in teams
  • Commitment to the continual development of one’s cultural competence
  • Commitment to ongoing professional development


  • A passion for organization; the ability to work within administrative systems and create new systems where needed
  • The ability to engage thoughtfully with parents and families about challenging topics, including those that arise in regard to learning differences
  • People management: The ability to manage groups of people effectively, be they families, faculty, or students, empathically and maintain a healthy school culture
  • Time management: The ability to manage time and delegate responsibilities effectively
  • A knowledge of, and support for, project based learning and progressive pedagogy
  • A desire to collaborate: to strive for unity, harmony, and cooperation through tact, helpfulness, respect, and a recognition of individual differences and the special abilities and strengths of each fellow faculty member. 
  • A clear and coherent ability to relay the expectations, behavioral guidelines, and other information necessary to ensure that all constituencies are fully informed consistent with their individual roles 
  • Dedication to supporting innovative and nontraditional curriculum 
  • Comfort in a startup culture in which specific roles and responsibilities are in the process of developing



  • Learn about all the major elements of the school, including its history, mission, vision and core competencies to become acquainted with the school’s ethos by meeting with major stakeholders, including the CEO, Principal, faculty and parents
  • Learn about the day-to-day operations of the school by observing and/or shadowing a non-teaching faculty member
  • Learn about our early childhood and high school programs so that you can better see the developmental arc of our students
  • Participate in programs for the orientation of new faculty and in-service training of all faculty
  • Oversee the day-to-day operation of grades 2-7, including absences and leaves/substitutes, coaching new faculty, managing behavioral issues that arise among students, and division-specific meetings 


  • Take on the oversight of individual behavior and learning plans for second through seventh grade students
  • Conduct regular meetings with faculty which will deal with routine school matters
  • Engage with parents as stakeholders and work with them to manage the process of their children’s learning experience at Bennett Day
  • Function as the primary articulator of your division’s programs, expectations, behavioral guidelines, and other information necessary to ensure that all constituencies are fully informed and consistent with their individual roles
  • Participate in regular meetings with core faculty groups within the school, including the Learning Resource team and the Operations/Administrative team in order to effectively manage academic and logistical operations
  • Take the lead in the academic guidance of students in grades 2-7; maintain complete academic records on all students; oversee the pedagogy and methods used by teachers in measuring student achievement in relation to our developmental and competency map
  • Maintain awareness of the educational, physical, social, and psychological needs of the members of our school community in grades 2-7 and develop plans for meeting these needs
  • Attend admissions and marketing events as needed to share the school’s story to potential Bennett Day families
  • Act as lead in the process of ensuring that teachers in grades 2-7 are familiar with and adhere to school policies in all areas of the school operation.


  • Observe, supervise, and help evaluate grades 2-7 faculty in the development and implementation of curriculum; supervise the teaching process, and review and evaluate the academic programs
  • Make recommendations to the principal regarding the hiring and retention, and the grade-level assignment, of faculty in grades 2-7 
  • Present to prospective families at information sessions
  • Be a part of admissions events for the purpose of vetting of student applications for admissions
  • Oversee the interview and vetting process for middle years faculty 
  • Serve as a consultant/coach to teachers in matters of classroom management, teaching methods, and general school procedures.
  • Assist in the admission process for interviewing and evaluation of applicants for enrollment.


  • Help make enrollment decisions to finalize students for admission in grades 3-8  in the fall of 2022
  • Contribute to the master school class schedule and to assign teachers and students to classes and other obligations
  • Be a visible presence in all areas of the school; work toward a resolution of all problems – both routine and unique – as they arise in grades 2-7; keep the principal informed of the general programs, activities, and problems of the school.

If interested, please apply HERE!

Bennett Day School is an equal opportunity employer.

Athletic Associate

Athletic Associate

Position Purpose:  

Under the direction of the Division Directors and Director of Auxiliary Program, the Athletic Associate coordinates and coaches extracurricular athletic activity that fosters skill development, understanding of sports, and appreciation for a variety of athletic activities and programs, teaming, and sportsmanship for scholars and adults. The Athletic Associate role also provides physical education classes for 5th-11th grades.

Essential Job Functions:

  • Manages and communicates athletic facility schedule
  • Assists in the selection and training of coaches 
  • Schedules all high school athletic contests, including arranging officials for the contest, and maintains the proper and necessary records.
  • Arranges transportation for all away contests.
  • Supervises the preparation and verifies all athletic eligibility lists.
  • Supervises high school athletic contests and acts as the host to officials and visiting schools. Oversees the supervision of contest employees and volunteers who work the athletic contest.
  • Works with the existing Phys Ed team to order all equipment and maintains a current inventory of all athletic equipment.
  • Ensures adherence to medical and safety requirements.
  • Facilitates meetings with coaches and staff when necessary
  • Leads classes of Physical Education by creating lesson plans in collaboration with the Physical Education department.

Job Qualifications: (Minimum Education and Experience)

  • Bachelor’s degree (B.A.) or Health/Fitness Certifications 
  • Coaching/Leader Experience required
  • Prior successful experience working in education strongly preferred

Job Specifications:

  • Strong communication and interpersonal skills to communicate effectively with faculty,
    scholars, parents, and community organizations.
  • Ability to work evenings, weekends or irregular hours as necessary
  • Develops positive relationships with staff and scholars to encourage teamwork and collaborative
    decision making.
  • Imaginative thought process that encourages alternative and creative solutions to budgetary
    and staffing difficulties.
  • Excellent organizational, communication and interpersonal skills
  • Working knowledge of instructional technology and associated software tools
  • Ability to establish quick rapport with both scholars and adults
  • Ability to analyze data for the purposes of decision making and planning
  • Calm and patient demeanor with scholars and others

Job Requirements:

  • Physical strength to independently lift 20-25 lbs
  • Fluency in written and oral language in English
  • Ability to oversee and ensure the safety of children in and out of the classroom
  • Required immunizations to prevent communicable diseases

If interested, please apply HERE!

Bennett Day School is an equal opportunity employer.

Middle School Lead Teacher

Middle School Lead Teacher

Agreement Start Date: August 1, 2021

The Bennett Day Middle School is hiring a lead teacher. The Middle School Lead Teacher position is for an education professional eager to participate in the development of a growing Reggio-Emilia inspired academic program. Bennett Day School teachers understand that the craft of teaching is dynamic; they adapt to and integrate this belief in his or her daily work in the classroom and school community.  In this role, you’ll be responsible for helping to design and implement the core characteristics of our progressive, project- and competency-based middle school. Reporting to our Director of Intermediate and Middle School, you’ll bring your experience to build upon a brand new middle school that is true to our progressive mission.


As a lead teacher, you’ll design and teach courses, both in Project-Based Learning environments and through traditional intensives, based on the needs of our students and in your field of expertise. You’ll act as a mentor to new colleagues as our school grows in future years. Most importantly, you’ll act as advisor to the students in that first cohort, leading the students as a mentor through all elements of the school experience. As one of our founding teachers, you’ll be intimately involved in every aspect of the design of our school, and have input into every major pedagogical and/or curricular decision that the middle school makes. You’ll simultaneously develop your pedagogical and design skills free from many outside constraints, as you will be designing and implementing a project-based curriculum in a grade-free school. You’ll have the opportunity to develop meaningful educational relationships with students in your work as an advisor with a small section of students. You’ll also learn from your colleagues during the 5+ hours per week of professional development, which occur on Wednesdays when students are released early. 


  • 5+ years experience as a middle school teacher in STEM field
  • Experience as a mentor/advisor to adolescents within an academic setting
  • Innovative program and curriculum development experience; inquiry-based and/or project-based learning preferred
  • Demonstrated success in designing and teaching in competency-based, standards-based or standards-referenced learning programs
  • Collaborative mindset; adept at working with teams and open to new ideas
  • Deep engagement in pedagogical trends, research, and best practices
  • Commitment to continual development of one’s cultural competence
  • Flexibility and adaptability in teaching and collaborating in a remote or alternative environment
  • Education Background: a Bachelor’s degree; Master’s degree in education preferred


  • Grade-level curriculum development
  • Individual student documentation and evaluation
  • Family communication: home visits, conferences, blogging
  • Mentoring, collaboration and communication with Lead and Apprentice Teachers
  • Professional Development: Wednesday afternoon; beginning and end of year PD
  • Collaboration, communication, and integration with Specialist teachers (Art, Music, TESLab, Spanish,PE)
  • Participation in self-evaluation and reflection process; individual and team meetings with the Director of the Intermediate and Middle School
  • Participation in family/community evening/weekend events: Curriculum Night and Admissions/Marketing outreach events.
  • Participation in arrival/dismissal and/or lunch/recess duties as assigned
  • Responsibilities are not all-inclusive and may include other duties
  • Required immunizations to prevent communicable diseases


  • Learn about all the major elements of the middle school (currently in draft form) to become acquainted with the school’s vision
  • Learn about our competency-based education model AND software so you can better keep track of student progress
  • Teach us about what you believe might be worth changing or editing in those documents to better serve all students
  • Begin designing the School’s advisory program, complete with Social/Emotional curriculum and developmentally responsive checkpoints using materials from Responsive Classroom and Project Wayfinder for Middle School
  • Using your content knowledge, teach us what should be in the Middle School competency map (a list of all the major skills required of students) in your field(s)
  • Outline the first trimester intensive in your area of expertise (Math)
  • Meet with the Director of Intermediate and Middle School 1-2 times per week (working around your schedule and availability) to coordinate on mission and tasks

WITHIN SIX MONTHS (Through the first trimester)

  • Create, in collaboration with Middle School team, our first Project-Based Learning experience for students
  • Be a part of the planning for info sessions for prospective families
  • Be the content-area expert and most important voice in development in your field(s) of expertise 


  • Be a part of admissions events for the purpose of vetting of student applications for admissions
  • Support planning and delivery of professional development to colleagues in the intermediate grades

If interested, please apply HERE!

Bennett Day School is an equal opportunity employer.

Part-Time or Seasonal Positions:

Upper School Adjunct Teacher

Upper School Adjunct Teacher

Passionate about the work you do? Want to share that passion with young people? The Bennett Day Upper School is hiring adjunct teachers for the 2019-2020 school year. Bring your knowledge and experience into the classroom, sharing your passion as an adjunct faculty member in a progressive learning environment. Work with a flexible schedule and explore an opportunity to inspire others. Reporting to our Director of Upper School, you will be a part of a unique and growing school who is looking to change the way students experience school.


The Opportunity:

As an adjunct, we have two unique ways to get involved at Bennett Day:

  1. Subject-Based Seminars: You will be teaching a seminar in your area of expertise over the course of 12 weeks (one trimester). This would be considered “traditional” teaching, in the sense that the course will operate much like any high school or college course. The delivery of the seminar will require a mixture of meetings with the class 3 times per week, with each class period running 90 minutes. These meeting times can serve as:
    1. time for clarification based upon common questions that have been received during the week or questions students currently have.
    2. time to give direct instruction.
    3. time to work on an activity with students to reinforce student knowledge.

A typical week would include meeting with students during required times, providing feedback to each student, answering student questions in a timely manner, and managing online coursework.

  1. PBL Subject Teaching: Every student in our school takes a cross curricular, themed, Project Based Learning (PBL) experience every trimester. These PBLs are co-taught by our lead teachers, but require subject-level experts to help plan and implement content in specific areas of need. In this role, you would be bringing your expertise to the team for approximately 10-12 hours each week to:
    1. Help brainstorm and plan content relevant to student interest and content needs
    2. Create learning experiences for students in your subject as it relates to the theme of the PBL
    3. Lead students through activities related to the PBL

Weeks as a PBL Subject teacher may vary in terms of contact time with students and expected duties, depending on the needs of the specific PBL.

For both options, you will also be asked to assess students based on specific demonstrations of skills mapped to our competency-based system. If you are unfamiliar with competency-based learning, here is an article that explains it. We do not use A-F letter grades.

The Salary: $3000/course (each course=one trimester)

Expected Hours Per Week: 10-12



  • Knowledge of progressive education practices, such as project-based learning or Harkness/Socratic seminars
  • Demonstrated commitment to teaching in a competency-based learning programs
  • Commitment to the continual development of one’s cultural competence
  • Commitment to ongoing professional development
  • 2 years experience working with adolescents (ages 12-20) in an education setting
  • Commitment to attend the on-boarding process so as to become acquainted with Bennett Day’s methods and mission
  • Experience in or strong desire to work in a Project Based Learning environment


  • Experience designing learning experiences
  • Interest in the Science of the Adolescent Brain/Learning Science
  • Working knowledge of the field of design in education, especially design and systems thinking
  • Working knowledge of one additional language (desired, but not required)



Every adjunct teacher needs to complete a Bennett Day School orientation in order to understand the methods, assessment and pedagogy style employed by the school. This will occur over several days prior to the beginning of the trimester.

On-boarding is a training period to help those new to Bennett Day School to create a meaningful curriculum and assess students in a competency model. Adjuncts will bring their proposals as well as skills they expect students to gain to workshop the creation of coursework with competencies that fit the values of Bennett Day.

Each Bennett Day adjunct teacher must participate in an initial day-long in-person visit to the school to get to know the students.

To Apply:

  1. Submit a proposal relating to your area of interest. The proposal should include:
    1. If you are proposing a stand-alone course, please provide a sample of what your curriculum would look like week-to-week for the entire trimester. (*We understand that things change depending on student needs, but we would like to see an outline of what a student might accomplish), explicit skills a student could obtain by completing this seminar (see our competency map for initial guidance, although you could add your own as well), and a list of deliverables that can be added to a student portfolio
    2. If you are submitting to work on a PBL, please identify your area of expertise that you would bring to the PBL, an identification of the skills you think high school students would gain based on your involvement, and a link to any PBL work you’ve done in the past.
  2. Submit a cover letter and resume that describes your experience, and why you would be a good fit to teach your topic of interest.

If you’re interested please apply HERE.


Bennett Day School is an equal opportunity employer.

Substitute Teacher Position

Substitute Teacher Position

Bennett Day School is a progressive independent day school looking for passionate educators with an innovative spirit and rich background in early childhood, primary classroom, and school experience.  We are a new type of independent school; unabashed believers in the values of progressive education, we put students at the center of the process of learning.

The substitute teacher positions are for candidates eager to participate in and learn through the development of a new academic program.  The ideal candidate would have a flexible schedule that allows for pre-scheduled dates as well as day-of requested dates. Substitute teachers help support classroom learning and school culture.  Bennett Day School fosters a collaborative work environment where a substitute will support an authentic learning place for all students. 

Job Qualifications:

  • Experience in early childhood and/or elementary classrooms
  • Creative spirit
  • Collaborative mindset; adept at working with teams and open to new ideas
  • Experience with technology use and applications
  • Adaptability
  • Education Background: a Bachelor’s degree or working towards a degree is preferred
    • Early childhood and elementary coursework required

Job Requirements:

  • Physical strength to independently lift 10-15 lbs
  • Fluency in written and oral English language.
  • Ability to oversee and ensure the safety of children in and out of the classroom

Job Specifications:

  • Direct classroom work with children ages 4 to 7 years old
  • Work collaboratively with lead teacher in all aspects of classroom life
  • Recess and gross motor play supervision
  • Support and model positive discipline
  • Support family style eating
  • Possible Hours:  
    • M/T/Th/F: Full day 7:30 – 4:00, Half day 7:30 – 1:00 or 12:00-4:00, AfterCare until 6:00
    • Wednesdays: 7:30-1:00, AfterCare until 6:00

If interested, please apply HERE!

Bennett Day School is an equal opportunity employer.

Bennett Labs Positions:

General Inquiry:

General Inquiry Application

Bennett Day School is always looking to attract employment inquiries and develop relationships with other educators and faculty who are drawn to our mission and vision.

If you are interested in applying for a position at Bennett Day School, but do not see the perfect opening to fit your needs, we are happy to have you complete a general inquiry application that we can keep on file should a relevant position become available.

Along with the application, interested candidates should submit a cover letter and a current resume. No email or telephone inquiries, please.

Click here to submit your application.

Bennett Day School is an equal opportunity employer.

Bennett Day School is an equal opportunity employer.  All applicants will be considered regardless of race, color, religion, sex, national origin, sexual orientation, age, marital, or veteran status; disability; or any other legally protected status.  Equal access to the hiring process, services, and employment is available to all persons.