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Program Facilitator at Wallkill Correctional Facility

Defy Ventures
Wallkill, NY Full Time
POSTED ON 11/14/2025 CLOSED ON 12/22/2025

What are the responsibilities and job description for the Program Facilitator at Wallkill Correctional Facility position at Defy Ventures?

Program Facilitator, Wallkill Correctional Facility

Upstate NY, Hudson Valley

(Part-time Hourly, Non-Exempt)

About Our Work:

Defy’s entrepreneurial programs enable one of America’s largest forgotten communities to defy the odds. We equip our Entrepreneurs in Training (EITs) with new skills, new connections, and a new belief to match their new purpose, and succeed in their new life of economic independence. Defy works to address layers of racial injustice through our commitment to changing perceptions, breaking cycles of recidivism, and helping people to create equity in historically marginalized communities.

About Our Position

We are seeking a program facilitator for our CEO of Your New Life (CEO YNL) prison program. This holistic and confidence-building curriculum prepares incarcerated Entrepreneurs in Training (EITs) to rewrite their future with comprehensive employment-readiness, healthy habits, and entrepreneurship training during their incarceration. Cohorts are six to nine months long and class meets Tuesday and Thursday evenings from 5:30 – 7:30 pm, 2 times per week at Wallkill Correctional Facility. As part of our class, EITs will develop an understanding of the entrepreneurial journey culminating in a business pitch competition.

Our Prison Program Facilitator position is ideal for someone with a teaching, coaching and/or social service background who is comfortable with business and/or entrepreneurship topics and able to:

1) Work with diverse, incarcerated populations

2) Travel to the prison and facilitate classes inside

3) Build and maintain healthy boundaries.

Responsibilities

  • Act as the primary facilitator-coach of Defy Ventures’ CEO YNL curriculum 2x per week at Wallkill Correctional Facility (classes are in the evenings 5:30 – 7:30pm, Tuesday and Thursday)
  • 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 in a timely manner 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 two volunteer events over the course of each 6-8 month program
  • Attend training sessions as needed (minimum monthly, typically virtual)
  • Other duties as assigned

Requirements

  • 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
  • Teaching or group facilitation experience is a plus
  • Available to work part-time for a total of 8 - 10 hours per week (typically 2-3 hour class periods plus administrative support and/or training time)
  • 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 New York Department of Corrections and Community Supervision (DOCCS) to enter the prison facility
  • Reliable transportation and valid driver’s license

About Defy Ventures

Defy Ventures’ mission is to change mindsets to give people with criminal histories their best shot at second chance. We are working to cut the recidivism rate in half by leveraging entrepreneurship as a tool to increase economic opportunity and inspire personal transformation. Defy’s prison and post-release programs provides entrepreneurship, employment, and personal development training to support formerly and currently incarcerated people to successfully reenter society by obtaining meaningful employment and, when ready, to start a small business. 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 seek to build a redemptive, authentic community between EITs and our volunteer community. For more information on Defy Ventures, please visit defyventures.org.

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

Job Type: Part-time

Pay: $27.00 per hour

Expected hours: 8 – 10 per week

People with a criminal record are encouraged to apply

Experience:

  • facilitation or teaching: 1 year (Required)

Shift availability:

  • Night Shift (Required)

Work Location: In person

Salary : $27

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