Kewanee, IL
In-Person
People with a criminal record are encouraged to apply
Closing:
July 31, 2025

Defy Ventures: Prison Program Facilitator

Full job description

You are an excellent facilitator, skilled at building relationships, and are organized. You are comfortable working with vulnerable populations (e.g. those who have experienced trauma, mental illness, homelessness, substance dependency, incarceration, etc.). You’ve had experience teaching curriculum to a group and are comfortable creating an inclusive environment and a safe space for sharing. You are adept at keeping discussions constructive and positive, even in challenging situations. You have experience or believe you would be comfortable working with incarcerated individuals and with prison staff to keep Defy’s entrepreneurship, personal development, and career readiness program on track. At Defy, your task is to ensure that our prison program is facilitated meaningfully and successfully.

This part-time opportunity is ideal for someone with a teaching, coaching and/or social service background who is comfortable working with diverse, incarcerated populations. You will be trained to deliver Defy Ventures’ CEO of Your New Life curriculum, which is a personal development, career readiness, and entrepreneurship training program. Individuals with lived experience are encouraged to apply, with the understanding that you must be able to be cleared to enter the facility. The ideal candidate will live within 45 miles of Kewanee, Illinois.

Responsibilities

  • Act as the primary facilitator-coach of Defy Ventures’ 8-month CEO of Your New Life curriculum teaching classes 2x per week at Kewanee Life Skills Re-Entry Center.
  • Lead inclusive spaces for collaborative learning with groups of currently incarcerated adults, including working with graduates of the program serving as peer facilitators
  • Prep for weekly classes and ensure all necessary materials are accounted for, distributed and/or collected
  • Help answer participants’ questions about the program
  • Ensure assigned work is completed, logged, collected as required, and sent timely for processing
  • Communicate weekly with supervisor regarding class progression
  • Record class attendance
  • Assist with visit and event preparation (e.g., event needs, volunteer clearances, supplies, etc.)
  • Support Program Manager communication with prison staff to ensure participants receive the appropriate permission to attend all program classes and events
  • Attend and support approximately three volunteer events over the course of each 8-month program
  • Attend training sessions as needed (minimum monthly, typically virtual)
  • Other duties as assigned

Requirements

  • Strong group facilitation and/or teaching experience
  • Strong interpersonal and communications skills, with the ability to intelligently and credibly articulate Defy’s programmatic objectives and mission
  • Basic computer proficiency and ability to use Google email, calendar, docs and sheets
  • Collaborative team player with a "can do" attitude; willing to roll up sleeves and do whatever it takes to support Defy priorities
  • Available to work part-time 2 days per week (teaching 2 classes in the facility twice a week) plus administrative support for a total of 10-15 hours per week
  • Strong presentation and facilitation skills
  • A willingness to learn and deepen your facilitation practice and open to feedback
  • Excellent judgment and ability to maintain a professional demeanor and positive attitude, even in ambiguous situations and during high-pressure periods
  • Ability to receive necessary clearances from the Illinois Department of Corrections to enter the prison facility
  • Reliable transportation and valid driver’s license

Compensation

Hourly Rate of $24/hour

About Defy Ventures

Defy Ventures is an entrepreneurship, employment, and personal development training program that recognizes the potential in many formerly and currently incarcerated people to become successful, legal entrepreneurs. Entrepreneurs in Training (EITs) “defy the odds” through our program, which includes intensive leadership development, Shark Tank-style business pitch competitions, and executive mentoring. We work to address injustice through our commitment to changing perceptions, breaking cycles of recidivism, and helping people to create equity in historically marginalized communities.

Defy Ventures is an equal opportunity employer. Defy Ventures uses E-Verify to confirm the employment eligibility of all new hires in the United States. All applicants will be considered for employment without attention to race, color, religion, sex, sexual orientation, gender identity, national origin, veteran, or disability status.

To apply, applicants should email a resume and thoughtful cover letter with Prison Program Facilitator, Illinois in the email subject line to info@defyventures.org.

Job Type: Part-time

Pay: $24.00 per hour

Schedule:

  • Day shift
  • Evening shift

People with a criminal record are encouraged to apply

Work Location: In person

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