“Do the best you can until you know better. Then when you know better, do better.” 

-Maya Angelou


Paid Positions

Assistant Director & Social Worker

We are currently looking for an Assistant Director & Social Worker to begin in June 2019.

  • Flexible hours (part-time or full-time)

  • Salary determined upon experience

  • Deliver weekly social-emotional services to each Redwood Day student

  • Help develop and maintain Individual Learning Plans for each student

  • Directly work with Kait to develop Redwood’s mission, network, marketing, curriculum and parent support

  • Monitor all afternoon activities during the school year

FULL-TIME Administrative COOrdinator & Instructional Assistant

We are currently looking for a full-time Administrative & Instructional Assistant to begin in June 2019.

  • 40 hours a week

  • Exact salary TBD based on experience

  • Coordinate administrative activities including corresponding with clients, creating systems for classroom, networking with potential partners, creating materials for lessons, etc.

  • Give support to lead instructors in Wilson, Math, Science + Global Studies

  • Monitor student lunch & Specials classes

  • Keep Redwood Space clean

SUMMER CAMP Certified Wilson instructors

We are currently looking for Certified Wilson Instructors to help teach our Morning Intensive Camp (June 24-August 1, Monday-Thursday, 8:30-11:00 am) and our Wilson Small Groups (June 17-August 8, Monday/Wednesday OR Tuesday/Thursday, 4-6 pm)

  • 6 Weeks of Morning Intensive Camp: $4000

  • 8 Weeks of Wilson Small Groups: $2000

  • Paid Training Day + Paid Report Writing Day

  • 1099 employee

  • All sessions @ our office (7007 N Glenwood Avenue)

  • Will implement small-group Wilson lessons

  • Must be a Level I or II Certified Wilson Teacher

If you are interested in any of the above positions, please send the following to kait@redwoodliteracy.com. Please reach out with any questions regarding the application process. We're looking forward to meeting you!

  • Resume

  • Cover letter explaining your previous Wilson and other teaching experience

  • 2-3 Letters of Recommendation


Whether you are looking to invest an hour a week into bettering Chicago, are passionate about literacy and want to inspire young learners, or need some volunteer hours, we could always use an extra hand. Please contact us at info@redwoodliteracy.com to inquire about the best use of your specific skills, time and passion in encouraging learners on their journeys.

Donate Books & Supplies

We are building our library and are always looking for new titles to add to our collection of high-interest texts. If you have some quality books to give away, please stop by! 

We go through hundreds of sticky notes and index cards every month and are always seeming to run out of whiteboard markers. If you have some extra school supplies lying around, we promise we will love them well.

Sponsor a Student

Our mission is to build a self-sustaining business model where the highest quality instruction is offered at an accessible price point. While we continue to find our feet in this endeavor, your donation of any amount can be applied to a student's tuition to make it possible for them to attend and/or help alleviate the financial burden long-term, frequent intervention can be for families of various income levels. Please email us at info@redwoodliteracy.com or give us a call at 312-813-5141 if you would like to donate.