Technology Coach

BreakFree Education IRAA 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. 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. The first cohort has an intended start date of September, 2021. The BreakFree Fellowship is unique, and designed to be a national model demonstrating how to successfully support returning citizens.


The core of the 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 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.  Additional information about the Fellowship and the technology  training framework can be found on our website.



The Position:  We are excited to bring on a Technology Coach for the BreakFree Education IRAA Fellowship.  This is a unique position that combines:

  • Leading BreakFree’s technology, digital media and communication training for Fellows

  • Serving as BreakFree’s technology liaison to the Host Organizations who are hiring and providing the immersive training experience to the Fellows

  • Supervising a small team of Technology Guides who will offer real-time and ongoing one-on-one technology training and support to the Fellows

  • Supporting the Fellows by connecting them to community-based supports as they navigate a range of challenges related to transitioning from years of incarceration (housing, transportation, counseling)


The IRAA Fellowship is based in Washington, DC. All of the Host Organizations where Fellows will be working are located in the Washington, DC area.  The Technology Coach would likely need to be in DC for the first 6-8 weeks of this project, but afterwards might be able to work remotely or partially remotely. Lastly, we believe the Technology Coach may do some travel as a part of broader work of BreakFree Education, as well. 


The Technology Coach will earn a competitive salary and will be eligible for BreakFree’s healthcare and other benefits, on par with all full-time employees.


We are looking for the Technology Coach to start in mid-July, 2021; the first cohort of Fellows will start in September, 2021.


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

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

  • Truly believes that all adults can succeed and thrive in the workplace, with the right training and support, and that returning citizens deserve the chance to pursue work they are passionate about, where their voices matter.

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

  • Is eager to learn, open to making mistakes, is a team player who believes in collaboration and supporting each other, and who is honest and candid.

  • Who is a self-starter who can function efficiently without constant supervision, who is a creative problem solver and doer.

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

  • Is flexible and open to supporting people with a wide range of skills and needs, and to working ‘odd’ hours to fit the needs of ‘clients’


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

  • Has excelled as an adult technology trainer or coach, both in-person and remotely, with a preference for someone who has provided technology-related training to beginning or reluctant technology learners

  • Is curious about and has an affinity for technology

  • Has earned a range of certifications including some or all of the following: Google Certified Level 1 and 2, Google Certified Trainer, Microsoft Innovator Educator, Microsoft Innovative Educator Trainer, Apple Certified Teacher, ISTE Certified, and Adobe Creative Educator Level 1 and 2

  • Is facile with a range of office productivity and communication software such as Microsoft 365, Google Workspace, Apple iWorks, Wix, Canva, MailChimp, Slack, Evernote, Zoom, and popular social media platforms

  • Has experience working with, training and supporting adults in immersive work and learn environments

  • Has successfully managed others, working in small teams

  • Holds a Bachelor’s Degree or equivalent (preferred but not required) 


Responsibilities will include but not be limited to:

  • Technology Training --The Technology Coach will be the lead technology trainer for the BreakFreeFellows. This will entail developing and leading an intensive four-week immersive training program designed to to ensure Fellows have an understanding of the basic technology tools needed to use on the job, leading ongoing technology training for Fellows throughout the duration of the Fellowship, and offering site-based technology training and troubleshooting that meets the needs of Host Organizations and Fellows. This work will be supported by a team of part-time Technology Guides, each of whom will be matched with a Fellow.  The Technology Coach will supervise and support the Guides.

  • Workplace and Transition Support--All of the Fellows are returning citizens who were incarcerated 15 or more years.  In addition to providing technology training, the Technology Coach will be a key member of the BreakFree team offering a series of “Welcome to the Workplace” training modules, providing individualized support to Fellows and Host Organizations around Fellows’ transition to the workplace, and facilitating the Fellows accessing critical support from other community-based programs.

  • Supporting the technology needs of BreakFree Educations’ ‘central office’-- We have a small central office that has basic technology upkeep needs as well as social media and communication support. Responsibilities in this area may include website, Twitter, Facebook, Linkedin, Google admin console, and general digital security.  

  • Modeling--The Technology Coach will be expected to model 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 Technology Coach will need to contribute their talent, creativity and passion to enhance the range of tools and supports BreakFree can offer, both through the Fellowship and our other work around the Country.

  • Understanding and committing--The Technology Coach 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 Technology Coach must be timely to work, must read and respond to emails and staff communications carefully, on time, and must complete other administrative responsibilities thoroughly and with attention.  


Salary and Benefits:

BreakFree Education offers a competitive salary and benefits package.  BreakFree Education offers a Simple IRA plan for all staff, and provides a 3% employer contribution once staff has worked for six months. BreakFree Education provides health care coverage for all staff and covers approximately 80% of the monthly premiums and 50% for dependents of employees.  This position is a 12 month, full-time position. 



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: June 10, 2021