A Second Chance: How Tech Can Create Career Pathways for People Returning from Incarceration

September 12, 2022  • Beth Semel & Rework Reentry

When released from incarceration, people may be “out,” but they’re not yet free. Laws exist at every level of government to prevent them from finding meaningful careers. The estimated unemployment rate for people returning from incarceration is 27%, higher than it has ever been for the general public.

In 2018, with support from Slack, The Last Mile, W.K. Kellogg Foundation, and FREEAMERICA, Next Chapter was founded with a bold mission: train and mentor people returning from incarceration to become coders at some of the world’s most respected tech companies. These are not just jobs. They are careers, and they can transform the lives of those employed, their families, and their communities. 

There are substantial benefits, corporate and societal, to helping people returning from incarceration get a second chance. To be successful, however,  companies need to take the time to understand the serious nature of this work and implement possible reforms to internal policies, workplace culture, and attitudes toward complex and weighty issues like race and the concept of redemption.

To help companies navigate the process for hiring and supporting people returning from incarceration, the Aspen Institute and Slack have just launched a new Playbook. It breaks down everything from legal and HR hurdles to the human elements of making hiring programs a long-term success. Divided into discrete, bite-sized content, the Playbook makes it easier for companies to answer the question, “Where to begin?”

REad the Playbook

Read on for the highlights.

Why should tech companies consider this? What are the rewards?

  • With a significant skilled worker shortage in the tech industry, training and hiring people returning from incarceration can help fill much-needed gaps in talent acquisition.
  • The Next Chapter network has proven that people returning from incarceration have the ability to become talented coders with the right pre- and post-release training. These individuals also make good employees, bringing valuable and durable skills that are well-suited for growth within a company. These include problem-solving and de-escalation, emotional intelligence, loyalty and high retention, and perseverance.
  • Tech companies have the opportunity to lead and make a substantial impact: the business community already looks to technology companies as innovators. The higher salaries and quality of jobs the industry provides can create transformative change for employees as well as their families and communities, setting a new standard in business.
  • Hiring programs demonstrate that a company cares about justice, equity, inclusion, empathy, second chances, and resilience, as well as challenging traditional notions of who is deserving of opportunity. This work can lead to increased loyalty and retention of all employees who appreciate working for a company that acts on its values.

What should companies think about when considering building a program for hiring people returning from incarceration?

  • While there are laws at every level of government that act as barriers to finding gainful careers for people returning from incarceration, major companies have found ways to work around these obstacles to provide transformative career paths. The hurdles can feel bureaucratic, but they deeply impact people’s lives, and can be overcome with focus and effort.
  • Building a successful hiring program will take internal policy adjustments, evaluation of work culture, and substantial company-wide education.
  • Additional trauma-informed support and mentorship is required for each employee; working with a community-based third-party reentry organization is the best approach.
  • There are huge gaps between perception and reality when it comes to risk. No companies have reported security or safety incidents, whether physical or digital.
Potential Challenge Solution
A company has no policy in place to consider the context if a person fails a background check. Create a policy that escalates any flagged background check results to a leadership team that has an evaluation framework like “time-nature-time” and invites the person to provide context.
Leadership and staff are worried about personal and information security. Once companies establish educational opportunities and person-to-person exchanges between staff members and people returning from incarceration, worries often evaporate. Long-term employment and appropriate supports have been shown to reduce recidivism, and partnering with a third-party reentry support organization can help ensure that appropriate individualized assessments are made.
Pre-existing contracts or interpretations of laws in your jurisdiction prohibit people returning from incarceration from working with customer data. Restructure backend systems and development processes to allow for sufficient compartmentalization, and give employees the ability to work securely.
A person returning from incarceration may need additional support to help with mentorship, housing, social services, trauma-informed care, and other reentry challenges. Engage a third-party reentry organization, like Next Chapter, to help provide informed support and handle the care that companies may not be equipped to handle.
The person returning from incarceration needs specialized training and on-the-job experience to finish their education. Partner with a training organization or boot camp to provide specialized curriculum that meets the company’s needs. A company can also bring the person on for a time-limited apprenticeship phase where they learn on the job and work towards established milestones of performance.


This sounds like a lot of work, and it is. But it’s worth it. At its most simple, the task is this: embrace individuals who are seeking a second chance, and help them to learn and be productive within the company. Support them, and take care to adapt to their specific needs. If this is done, companies can change lives and make their community, and the organization, better for it. 

Download a shareable version of this summary here. Read the Playbook.

The Rework Reentry Playbook is based on an analysis of real-world efforts to train and hire people who are formerly incarcerated into technology careers. Aspen Digital conducted interviews with over 40 people, including executives and staff from six major tech companies that have successfully hired people returning from incarceration as well as reentry and workforce development experts from 13 different nonprofits and foundations, many of whom have themselves returned from incarceration. The tech company interviewees represented departments including human resources; legal; risk and compliance; engineering; diversity, equity, and inclusion; social impact; and talent recruitment.

A collaboration of Aspen Digital, the Aspen Criminal Justice Reform Initiative, and Slack, Rework Reentry seeks to identify and help eliminate systemic barriers to meaningful tech careers for people returning from incarceration. The effort engages returning persons, community leaders, and company executives through research-driven public education, convenings with key stakeholders, and documentary storytelling.