Prison Program Associate

Job Type

Part Time




United States


(Part-Time Position)

You are organized, skilled at building relationships, and an excellent facilitator. You are comfortable working with populations who’ve experienced trauma, mental illness, homelessness and/or substance dependency. You’ve led groups 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 are encouraging and can “roll with resistance.” You believe you would be comfortable working with the incarcerated and with prison system authorities to keep Defy’s program on track. At Defy, your challenge is to ensure that our in-prison program is executed successfully.

We look for the following when evaluating new teammates:

  • Culture fit: You love our ambitious/spirited culture that is passionate about redeeming lives and restoring communities. We strive to display heart, empathy, and resolve in our daily interactions with one another.

You will be entrusted with your own share of responsibility and will work independently. You will have the support of teammates who look out for you and want you to succeed. 

This opportunity is ideal for someone with an educational and/or social service background who is comfortable working with diverse populations.


Duties include:

  • Supervising classroom activities (e.g., video watching, peer group discussions), typically 3-4x per week (typically evenings, may include weekend day at some facilities) at 1- 3 regional facilities
  • Lead the “Commitments and Affirmations” at the beginning of each class session
  • Remove any EITs (Entrepreneurs in Training) who pose disciplinary problems and report removals to Defy’s Prison Program Manager via updating roster
  • Help answer EIT questions about the program
  • Ensure return packs and Defy Journals are completed at each class session
  • Communicate weekly with Defy’s Prison Program Manager regarding class progression
  • Send weekly class roster and provide brief explanation for any attrition (e.g., disciplinary, transfer, dropout, release)
  • Assist with visit and event preparation (e.g., event needs, volunteer clearances, Prison Program Manager’s visits, supplies, etc.)
  • Work with prison staff to ensure ducats are issued to EITs for all program functions
  • Meet with Prison Program Manager weekly (via phone)
  • Meet with appropriate correctional staff on each prison visit
  • Attend approximately three volunteer events over the course of each 6-8 month class session
  • Other duties as assigned


  • Strong interpersonal and communications skills, with the ability to intelligently and credibly articulate Defy’s story and mission
  • Teaching experience or a Bachelor’s in Social Work, MSW, or other related degrees is a plus
  • Collaborative team player with a "can do" attitude; willing to roll up sleeves and do whatever it takes to support team priorities
  • Available to work part-time (2-4 evenings/weekend days per week), typically 2-4 hour shifts for a total of 10-20 hours per week. Assignment starts in January 2018
  • Strong presentation and facilitation skills
  • Excellent judgment and ability to maintain effectiveness, professional demeanor, and positive attitude, even in ambiguous situations and during high-pressure periods


About Defy Ventures

Defy’s is driven to level the playing field and to bring redemptive opportunities to America’s biggest underdogs. Our hatred of injustice fuels our impatience. We have a plan to scale to 21 new Chapters in the next six years, and to serve 10,000 incarcerated men, women, and youth in the next three years.

America is touted as the land of opportunity and second chances—a land of liberty and justice for all. But this isn’t the case for the 100 million Americans with criminal histories, who remain permanently stigmatized. Today, 30% of 23-year-olds have records.

Defy Ventures is a national entrepreneurship, employment, and character development training program that recognizes the potential in many former drug dealers and gang leaders to become successful, legal entrepreneurs. We “transform the hustle” of our formerly incarcerated Entrepreneurs-in-Training (EITs) by offering intensive leadership development, Shark Tank-style business pitch competitions, executive mentoring, financial investment, and startup incubation. We build a life-giving, authentic community between EITs and our executive volunteers as they bond in their humanity through their collaboration along the entrepreneurial journey.

Leveraging technology, we’ve created a “blended learning” model that holds the promise of scaling globally to revitalize the most underserved communities. We combine video-based training with in-person mentoring and events. Our online instructors include underdog-loving influencers like Randy Komisar (Kleiner Perkins), Tim Draper (Founder, Draper Fisher Jurvetson), Duncan Niederauer (CEO, NYSE), five Harvard Business School professors, two Stanford Business School professors, and Seth Godin (marketing guru).

Since its founding in 2010, Defy has served 2,000+ EITs across 18 states and 20 correctional facilities, and engaged 4,300+ executive volunteers. Defy has incubated 166 of its graduates’ companies, which in turn have created more than 350 employment opportunities for people in their communities. Grads report a 95% employment rate, and Defy’s recidivism rate to date is less than 5%. (Nationally, 76.6% of people are rearrested within five years of release.)

Defy has earned the trust of funders like Kapor Center for Social Impact, Silicon Valley Bank, Peery Foundation, Porticus Foundation, Sorenson Impact Foundation, Techstars Foundation, Google, eBay, TD Bank, Capital One, Bloomberg, LinkedIn, Yelp, and American Express. Defy has been showcased in national media including The New YorkerThe New York TimesThe Wall Street JournalForbes.comThe Harvard Business Reviewand Tech Crunch.

Defy’s Founder and CEO, Catherine Hoke, is an Ashoka Fellow, and was named by Fast Company as one of the 100 Most Creative People in Business. Defy is her second chance; here is a 4-minute video of Defy’s founding story, produced by Sheryl Sandberg’s Option B team:


Quick references:

Professional Level

None specified

Minimum Education Required

No requirement

How To Apply