Summer Intervention Specialist (In-Person, North Chicago)

Summer 2025 Intervention Specialist 

1099 Contractor Position 

In-Person - North Chicago

• Continue making a difference in students’ lives this summer while still enjoying the magic of a Chicago summer by only working until 1:00 PM.
• Competitive pay
• Redwood provides all training and curriculum materials (all teaching materials belong to you and go home with you after the summer)! 
• All new instructors receive FREE instructional coaching 
• Daily support from your Site Director and fellow team of educators

Don’t just take it from us!

“I absolutely love being a summer instructor at Redwood Literacy! Teaching over the summer allows me to blend my passion for literacy with the chance to grow and enhance my skills as an educator. Each summer, I have the opportunity to get to know and teach new students from all over the Chicagoland area, expanding the reach of both my instruction and Redwood's incredible programming to make a lasting impact beyond the classroom during the school year. Redwood cultivates a positive, collaborative, and fun atmosphere, making it a rewarding place to work.” 

- Kaitlin L. (7-Time Summer Intervention Specialist )

About Redwood

Redwood exists so that all students with literacy struggles can access their dreams. By cultivating hope and restoring confidence, we help students dramatically improve their literacy, writing,  and math skills regardless of socioeconomic background or learning differences. 

Redwood has run Summer Morning Intensives since its inception in 2018, and we are excited to be heading into our eighth summer of programming. We are seeking highly qualified educators who are excited to be part of a team committed to fostering academic and social-emotional growth among a community of students by delivering targeted instruction and responding to student data. 

Job Description

Programming Details:

• Required  on-site training dates: June 17th & 18th, 9:00-4:00 PM CST
• Programming dates: June 23rd-July 31st, 8:30-1:00 PM CST (Monday - Friday)
• Instructors are expected to arrive by 8:00 AM CST 
• Please plan to bring your own lunch (instructors are expected to participate in monitoring students during the lunch break)
• No programming on July 3rd & 4th
• Onsite report writing day on Friday, August 1st (no students)
• Locations: You will be assigned to either Redwood’s Rogers Park OR Lincoln Park summer programming location for the full 6 weeks based on your preferences and Redwood’s needs.
• Content: During the 6-week summer program, you will be assigned to teach ONE of the following curricula based on your skills and preferences and Redwood’s needs. 
• Reading: Wilson Reading System® (must be WRS® Certified)
• Writing: Writing Our World™ (written expression & reading comprehension & AT)
• Math: Chris Woodin Math Strategies®
• Training: You will be required to complete two phases of training to prepare for summer programming.
•  #1 Asynchronous Onboarding: You will be assigned virtual training modules to complete on your own time between your date of hire and June 16th, 2025. The modules include:
• HR & Payroll 
• Intro to Redwood’s history and organizational culture 
• Logistics of what  makes a successful Redwood session
• Intro to the specific curriculum you are teaching 
• Progress monitoring and data tracking expectations regarding student growth and report writing 
• #2 Onsite Training: You will be required to attend onsite training days June 17th and 18th in either Rogers Park or Lincoln Park from 9:00-4:00 PM CST
• Meet  your site manager & team 
• Set up  your classroom 
• Be assigned and review student caseloads
• Prepare lesson plans based on your specific curriculum
• Review expectations and logistics for the summer program 

Responsibilities: 

• Completing Phase 1 & Phase 2 of onboarding by the assigned deadlines.
• Teach 22.5 hours a week of targeted intervention to small groups of students.
• Caseload:  20 students divided into groups of 3-5 students each. 
• Record progress monitoring, attendance, and engagement data for students after each day of programming via Pearl (Redwood’s Tutor Management System)
• Read, internalize, and respond to weekly team communication.
• Respond to parent and team communication within 24 hours, Monday through Friday, and reach out to your Site Director for support if needed.
• Complete all action items regarding preparing, writing, and sending progress reports to parents midway through the program and at the end of the program. 
• Administer provided assessments to each student in your caseload at the beginning and end of the summer and enter data into Pearl (Redwood’s Tutor Management System).

Compensation: $6,250 Stipend 

• Payment will be initiated in three equal installments upon meeting the necessary requirements.
• Installment #1:  July 9, 2025 
•  Installment #2: July 23, 2025 
•  Installment #3: August 6, 2025 (payment is dependent upon completion of student progress reports) 
• Substitute Policy:
• Please provide Redwood with a list of predetermined days on which you will require a substitute during the six-week program.
• If you need a last-minute substitute, please let your Site Director know as soon as possible, and they will assist in providing one. 
• All days requiring a substitute will be deducted from your upcoming payment installment (at a flat rate per day).
• Attendance Policy:
• Redwood has a zero-tolerance policy for no-shows or a pattern of tardiness. 
• Barring unforeseen circumstances, $50 will be deducted from your upcoming payment installment if tardy, and/or  Redwood may terminate this service agreement if the instructor is a no-show.  

Skills & Competencies:

• Required Credential: Instructors must be a certified teacher
• Passionate about deepening pedagogical knowledge and best practice implementation skills in all things literacy or math instruction.
• Enjoys students and seeks to see them grow in their academics and understanding of self.
• Robust understanding of Gmail, Google Calendar, Google Drive, Google Documents, and Google Sheets for admin tasks.
• Behavior management skills in small group settings.
• Excellent written expression skills.
• Ability to internalize and respond to student data to provide targeted and effective instruction.
• Deep understanding of and alignment with the mission of Redwood Literacy.