Upper School Mathematics Teacher

Bennett Day School Inc•Chicago, IL

About The Position

Bennett Day School is a progressive independent day school looking for passionate educators with innovative spirit and rich background in adolescent 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. The Bennett Day School is hiring a full-time lead teacher with an expertise in Mathematics. In this role, you’ll be part of the Middle and Upper School faculty team and be responsible for implementing the core characteristics of our progressive, project- and competency-based middle and upper school. Reporting to our Director of Middle and Upper School, you’ll bring your experience to the team to lead a cohort of students as part of the upper school team of teachers beginning in the fall of 2026-2027. Most importantly, you’ll act as advisor to the students in a cohort, leading a group of ten as a mentor through all elements of the school experience. As a teacher, you’ll also design and teach courses, both in Project-Based Learning environments and through traditional seminars, 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. THE OPPORTUNITY As one of our teachers, you’ll be intimately involved in every aspect of our growing school, and have input into major pedagogical and/or curricular decisions that the high school makes. You’ll simultaneously develop your pedagogical and design skills free from many outside constraints that you find in traditional schools, as you will be designing and implementing a project-based curriculum in a grade-free (no A’s, B’s or C’s) school. You’ll have the opportunity to develop meaningful educational relationships with students in your work as an advisor. You’ll also learn from your colleagues during the 5+ hours per week of professional development, which occur on Wednesdays when students are working with specialists. We are a small team and collaborate constantly on pedagogy, educational design, and student support. This position is ideal for someone who thrives when given the opportunity to make close connections and develop relationships with students, families and colleagues. YOUR FIRST YEAR: WITHIN ONE MONTH YOU’LL Learn about all the major elements of the middle upper school and how they embody the school’s mission and vision Learn about our competency-based education model, especially as it relates to mathematics Learn about our advisory program and work with your mentor teacher(s) and school counselor to plan your advisory Meet with the Upper and Middle School math team to coordinate on planning Create, in collaboration with the Upper School team, your initial design for a problem-based, inquiry driven and differentiated mathematics experience Plan for and meet your first group of advisees and their families WITHIN THREE MONTHS YOU’LL Teach your first classes as a member of the Middle/ Upper School team Submit regular reports on student progress Participate in our professional development program on a weekly basis Teach us about your vision for how mathematics might further integrate into our Project-Based Learning courses Chaperone (along with the entire US team) the Upper School retreat Lead conferences with families of your students Maintain a competency assessment of each student in your courses Attend admissions and marketing events as needed to share the school’s story to potential Bennett Day families WITHIN SIX MONTHS YOU’LL Write narrative assessments of your students and help them develop their own learning portfolios Be a part of admissions events Attend at least one professional development experience to learn more about at least one area of our pedagogical model with which you feel you need assistance or guidance Chaperone events on an as-needed basis Be the content-area expert and an important voice in development in your field(s) of expertise WITHIN ONE YEAR, YOU’LL Continue to teach math courses in addition to possible Project-Based Learning courses Contribute to the interview and vetting process when/if any additional faculty is hired Provide input on the curriculum for the 2027-2028 school year Responsibilities are not all-inclusive and will include other duties as assigned

Requirements

3+ years experience working with adolescents in an education setting focused on Mathematics
Recognition that your primary role is an advisor and that your content expertise is secondary to the position
Belief and/or experience in detracked math courses that implement effective differentiated instruction
Experience teaching math courses in a Middle and/or Upper School setting
Success in, or deep interest in, designing and teaching project- or problem-based learning and competency-based learning programs
Interdisciplinary and/or team teaching experience
Interest in/Experience working in teams
Successful experience working as a mentor/advisor to an adolescent within an academic setting
Interest in/Experience designing innovative and experimental curriculum in a collaborative setting
Commitment to continual development of one’s cultural competence
Commitment to ongoing professional development
Polymathness: having wide ranging interests and experience across different content silos (you would be interested in and capable of teaching both Math and Science, for example)
Dedication to designing innovative and nontraditional curriculum

Nice To Haves

Comfort in a highly collaborative, team-based culture
Experience with and enthusiasm for inquiry-driven mathematics pedagogy models
Experience or education in, or professional passion for, multiple content areas across traditional silos
Experience designing online learning experiences
Interest in the Science of the Adolescent Brain/Learning Science
Working knowledge of one additional language (desired, but not required)

Responsibilities

Lead a cohort of students as part of the upper school team of teachers beginning in the fall of 2026-2027
Act as advisor to the students in a cohort, leading a group of ten as a mentor through all elements of the school experience
Design and teach courses, both in Project-Based Learning environments and through traditional seminars, based on the needs of our students and in your field of expertise
Act as a mentor to new colleagues as our school grows in future years
Learn about all the major elements of the middle upper school and how they embody the school’s mission and vision
Learn about our competency-based education model, especially as it relates to mathematics
Learn about our advisory program and work with your mentor teacher(s) and school counselor to plan your advisory
Meet with the Upper and Middle School math team to coordinate on planning
Create, in collaboration with the Upper School team, your initial design for a problem-based, inquiry driven and differentiated mathematics experience
Plan for and meet your first group of advisees and their families
Teach your first classes as a member of the Middle/ Upper School team
Submit regular reports on student progress
Participate in our professional development program on a weekly basis
Teach us about your vision for how mathematics might further integrate into our Project-Based Learning courses
Chaperone (along with the entire US team) the Upper School retreat
Lead conferences with families of your students
Maintain a competency assessment of each student in your courses
Attend admissions and marketing events as needed to share the school’s story to potential Bennett Day families
Write narrative assessments of your students and help them develop their own learning portfolios
Be a part of admissions events
Attend at least one professional development experience to learn more about at least one area of our pedagogical model with which you feel you need assistance or guidance
Chaperone events on an as-needed basis
Be the content-area expert and an important voice in development in your field(s) of expertise
Continue to teach math courses in addition to possible Project-Based Learning courses
Contribute to the interview and vetting process when/if any additional faculty is hired
Provide input on the curriculum for the 2027-2028 school year
Responsibilities are not all-inclusive and will include other duties as assigned