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Technology Guide
BreakFree Fellowship 

About BreakFree Education: At BreakFree Education our mission is to radically improve education in the juvenile and adult correctional systems by investing in the potential and dignity of confined and recently released students of all ages. We develop quality educational programs that inspire and engage students held in confinement, and then support them upon release. We partner directly with juvenile and criminal justice agencies across the country, providing the resources, training, and networks they need to make school relevant and meaningful, so students can build a successful life when they leave. We started and continue to support the Travis Hill School in New Orleans, where young people held in the adult jail and juvenile detention center work towards their high school diploma. We also work with policymakers to shape the world we want to see – one where these young people have the education and support needed to reach their full potential.

The BreakFree Education IRAA Fellowship:

The Fellowship matches returning citizens who want to work in social and criminal justice reform with leading local and national nonprofits. The Fellowship is an 18-month, immersive, paid, on-the-job training program designed to result in permanent, long-term employment for Fellows and more representative, capable organizations. Fellows have all been incarcerated for 15+ years or more, for crimes committed as teens or young adults. This cohort has an intended start date of March 2022. The BreakFree Fellowship is unique, and designed to be a national model demonstrating how to successfully support returning citizens.


The core of our full-time IRAA Fellowship is our 18-month immersive, on-the-job- training centered around office productivity, digital media and communication tools essential for professional advancement in today’s workplaces. Our training is site-specific and tailored to ensure Fellows and host sites have the necessary support for Fellows to develop the skills to be successful, fully capable of delivering for their host sites. Our part-time Fellowship offers similar opportunities for Fellows to experience additional work and training while maintaining their current jobs. Our training ensures all Fellows develop competencies in core skills, with the support of BreakFree Education and their host sites and then, over time, develop more specialized skills that enable them to transition to full-time positions at their host site or elsewhere.  



The Position: 

We are excited to bring on a part-time Technology Guides for the BreakFree Education IRAA Fellowship. This is a unique position centered around providing one-on-one, real-time technology, digital media and communication training and support for Fellows. The Guide will be matched with a Fellow during an intensive training period designed to help Fellows develop their baseline productivity technology skills, so that they can enter the workforce in a prepared fashion. Through our program, the Fellow will be matched with a Host Site where they will work part-time. Prior to being matched, the Fellow will receive virtual training on technology and workplace readiness skills. 


The Guide will serve as a training partner for the Fellow, helping the Fellow develop their technology skills as they work on actual projects for their Host Organization.  Think of this role as a “guide on the side”, where you provide the Fellow with virtual support on projects that involve the use of technology. For example, if a Fellow needs to build a spreadsheet and is not familiar with some of the functionality the spreadsheet needs to be effective, the Fellow's supervisor, would reach out to the Guide who would offer real-time, remote training to the Fellow so that they can learn the skills needed to work on and complete the project. The goal of the Guides’ support is to ensure that Fellows learn the skills, and upskill where needed. 


In addition, the Guide will work with their Fellows on an ongoing basis to help them build technology skills as they work through a scaffolded technology curriculum developed by BreakFree Education and led by the Technology Coach. 

The Technology Guides will also be expected to adhere to expectations that we value at BreakFree Education.  This includes:

  • Modeling--Guides must demonstrate the sort of behavior we know is critical to creating an organizational culture built on hope and high expectations for achievement.

  • Pitching in and contributing--The Guides will need to contribute their talent, creativity and passion to enhance the range of tools and supports BreakFree can offer.

  • Understanding and committing--The Guides should be fully invested into what it means to work with returning citizens, including taking on roles and functions that extend beyond those outlined here.

  • Meeting basic administrative expectations--The Guides must be timely with their work, must read and respond to emails and staff communications carefully, on time, and must complete other administrative responsibilities thoroughly and with attention.


We anticipate the Guides working approximately 5 hours per week, after a start-up period where they may work closer to 10 hours per week.  Some of this time will be scheduled (for example, checking in with their Fellows at a set time for 1 to 2 hours on set days at set times), and some will need to be nearly ‘on-demand’ and real-time.  Guides will need to be available and responsive to Fellows and Host Organizations as technology needs arise in the workplace. You will work with your Fellow in order to figure out the best times that work with both of your schedules.


The IRAA Fellowship is based in Washington, DC. All of the Host Organizations where Fellows will be working are located in the metro Washington, DC area.  The Technology Guide work and provide support remotely.  

The Technology Guide will be paid as a W-9 contractor.


We are looking for the Technology Guide to start in early March 2022.


What We are Looking For--Beliefs and Values: We want to select a Technology Guides who: 

  • Are humble and self-aware: our Guides will be working with Fellows who have been incarcerated for 15 years or more;  our Guides must be supportive, caring and compassionate.

  • Are passionate about the role that technology skills can play in transforming the work and life opportunities for returning citizens.

  • Are flexible and open to supporting people with a wide range of skills and needs, and to working ‘odd’ hours.

  • Are experienced in andragogy and truly believe that all adults can succeed and thrive in the workplace, with the right training and support

  • Believe that returning citizens deserve the chance to pursue work they are passionate about, where their voices matter.

  • Are grounded in doing what is right and just, who are self-reflective, aren’t afraid to ask for help and who are willing and open to trying new and innovative ideas.

  • Are eager to learn, open to making mistakes, are team players who believe in collaboration and supporting each other, and who are  honest and candid.

  • Who are self-starters, who can function efficiently without constant supervision, who are creative problem solvers and doers.

  • Understand how critical it is to ‘get it done well,’ who are committed to worrying about and getting the details right, and who won’t quit in the face of frustration or challenge.


What We are Looking For--Skills and Experiences: We want to select a Technology Guides who: 

  • Have significant experience and are facile working with Google Workplace tools and MS Office tools, and are comfortable learning new technology skills such as Wix, Canva, MailChimp, Slack, Evernote, Zoom, and popular social media platforms

  • Have experience as a tutor or teacher in some capacity, with a preference for Guides who have experience training and supporting adults in immersive work and learning environments

  • Have experience working on teams and with people from a wide range of ages and backgrounds


Salary and Expected Hours:

This is a part-time, or contracted position. Our hourly rate will be between $15-20/hour for this position.  We anticipate the weekly hours needed for this work to be 5 to 10 hours per week.



BreakFree Education is an equal opportunity employer.  We believe that a diverse staff is a better staff.  Women, persons of color, and those directly impacted by the criminal or juvenile justice system are encouraged to apply to work with us at BreakFree Education.  For additional information about BreakFree Education, please visit our website at


Effective: February 21, 2022

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