Finalist
2021 Digital Workforce Challenge

The Last Mile

Team Leader
Sydney Heller
Solution Overview
Solution Name:
The Last Mile
One-line solution summary:
To provide opportunities for personal and professional growth for justice-involved individuals through education and technology training
Pitch your solution.

TLM is disrupting the system of mass incarceration in America by providing opportunities to justice impacted individuals to gain training and marketable skills. 

TLM offers a comprehensive vocational training program and wraparound reentry support to people who are incarcerated, providing a scalable model for change in a criminal justice system that is difficult to impact. Men, women, and youth are receiving technology training to become software engineers, achieving success that seemed impossible only a few years ago. TLM’s vocational training for high-demand jobs has proven to increase social mobility, open career pathways, and reduce recidivism.

The Last Mile has demonstrated through years of education and job placement that public-private partnerships and strong relationships with Departments of Correction can dismantle deep-rooted systems of oppression and counteract prejudice across entire industries. As a result, TLM has become the most requested prison education program in the country.

What specific problem are you solving?

Today, over 3,400 correctional facilities across the US incarcerate 2.3 million people. People of color account for approximately 37% of the US population, yet they represent 67% of the prison population. Post-incarceration, recidivism plagues our communities and poses an indomitable fiscal burden on the US society at large. 60% of people who are released return to prison within three years. 

A crucial factor that informs a sustained, successful reentry is gainful employment, and yet roughly 27% of the formerly incarcerated population is unemployed and an average of 19% are underemployed; about five times higher than that of the general population. The exclusion of formerly incarcerated job-seekers from the workforce costs the US an estimated $87 billion in lost GDP. (PPI)

While the unemployment rate is nearly five times that of the general public, formerly incarcerated individuals are more active in the labor market, with 93.3% of the incarcerated population working or looking for work compared to 83.8%. In short, this underserved population wants to work but less than 4% have a college education and only 25% have a high school diploma or GED, making the job application process extremely difficult especially for higher-paying jobs. (PBS)

What is your solution?

TLM offers a technical training program to people who are incarcerated, creating a scalable model for change. TLM’s program provides people with skills necessary to secure high-demand jobs and has proven to increase social mobility, open career pathways, and reduce recidivism. 

TLM has created a platform as a service (PaaS), which leverages several applications to deliver an in-prison web development program, all within an environment created by TLM specifically for incarcerated students without access to the internet.

TLM students across the country are taught remotely by instructors who video conference into in-prison classrooms to engage with students in real-time. Our platform includes a learning management system (LMS), asynchronous support via our Student Help Desk, and real-world software development tools such as GitLab and DevDocs. The TLM platform adheres to security requirements while serving as a central location for TLM instructors and staff to remotely interact with students, grade coursework, and track progress. 

After completing TLM’s program, individuals are qualified to apply for employment as full-stack programmers upon their release from prison. TLM is committed to solving the problem of recidivism in America through increasing access to education for incarcerated individuals and preparing professional industries to embrace fair chance hiring.

Who does your solution serve, and in what ways will the solution impact their lives?

TLM serves America’s incarcerated population, in turn also serving the marginalized communities from which most incarcerated individuals come from. Of the 2.3 million people incarcerated in the US, over 60% are from African American and Latino communities. The median pre-prison income among incarcerated adults is $20,800 -- over 50% less than the average US adult’s annual income.

TLM provides vocational training and post-release mentorship to individuals as a means of supporting successful reentry and ultimately preventing recidivism. By equipping those who are incarcerated with the hard and soft skills necessary for gainful employment after release, TLM offers individuals new career pathways that would not have otherwise been available to them. This has proven to prevent recidivism, as 0% of TLM graduates have returned to prison after their release. 

 Founded at San Quentin in 2010, TLM has grown and evolved based on input from current and formerly incarcerated people since its inception. The justice-impacted population is directly represented in our organization; roughly half of TLM staff are formerly incarcerated and contribute an active voice within TLM management and leadership teams. Additionally, TLM has launched an internal Web Development Education Apprenticeship. TLM hires former program participants post-release to provide academic support to current program participants, contribute to the curriculum, and continue their education and professional development. Apprentices are full-time TLM employees and earn a market wage salary while creating a portfolio of work and continuing to learn marketable skills. Further, TLM’s curriculum continues to be refined and expanded according to the feedback and performance of program students and graduates. 

Post-release, The Last Mile’s Reentry Department, a team of former program participants, supports the successful reintegration of returned citizens back into society, the workforce, and their families. We accomplish this by providing business and technology resources, as well as employment opportunities through our network of fair chance employers and referrals to community resources. We believe that lives are transformed through education, opportunity, and meaningful employment. Our goal is to create pathways for every TLM returning citizen to maximize their success. 

TLM understands that the successful reentry of returning citizens requires a holistic approach. Our participants have the technical skills to launch a fulfilling career. We provide workshops pre- and post-release to ensure returned citizens have the tools and resources to help them overcome the challenges that lie ahead. 

To better assist TLM alumni in their next journey, we conduct a reentry assessment which helps us support them in creating a tailored pathway for success. The reentry assessment is an evaluation of the participants’ desires, skills, and passion. This process includes a technical component that evaluates the participants' projects and technical abilities. This helps us to create learning pathways for those who would like to continue their education. 

The reentry assessment also includes a one-on-one interview, during which participants can share their continued learning goals and desired employment path. The assessment helps the reentry team provide each participant with appropriate resources. Based on the results of the assessment, the Reentry Department may offer a combination of the following resources:

  • Laptops and essential equipment for productivity

  • Continuing education opportunities 

  • Apprenticeship and internship opportunities

  • Referrals to a network of reentry referral organizations (eg. housing, transportation, benefits) 

To date, 85.14% of TLM returned citizens are employed full-time. In general, about 73% of the formerly incarcerated population is employed, with 19% working just part-time or seasonally. Our success in delivering our program remotely across men’s, women’s, and juvenile facilities and states underscores the potential impact we could have on individual lives and on the criminal justice system at large.

Which dimension of the Digital Workforce Challenge does your solution most closely address?
  • Reduce inequalities in the digital workforce for historically underserved groups through improved hiring and retention practices, skills assessments, training, and employer education and engagement
Explain how the problem you are addressing, the solution you have designed, and the population you are serving align with the Challenge.

To mitigate recidivism, TLM empowers incarcerated populations with modern skills, along with post-release mentorship, helping individuals secure gainful employment upon re-entering the workforce. TLM offers training in full-stack software engineering, in accordance with the market’s growing need for coders. As TLM evolves, the program will encompass job preparation for more high-demand fields, such as audio and video production, while also addressing reentry planning, a critical post-release component. Further, TLM will always include women’s, and men’s, youth facilities to create equitable access to training and skills.

Our solution will generate opportunities for a population that is underrepresented, underserved, and consistently underemployed.

In what city, town, or region is your solution team headquartered?
San Francisco, CA, USA
Is your solution already being implemented in one or more of the following ServiceNow locations (Australia/New Zealand, Canada, France, Germany, India, Ireland, Israel, Japan, the Netherlands, Singapore, the United Kingdom, United States), or are you planning to expand your solution to one or more of these countries?
  • My solution is already being implemented in one or more of these ServiceNow locations
What is your solution’s stage of development?
  • Scale: A sustainable enterprise working in several communities or countries that is looking to scale significantly, focusing on increased efficiency.
Explain why you selected this stage of development for your solution.

Our innovative approach to instruction and support post-release is tailored to fit the constraints of carceral environments and provide best-in-class education remotely and at scale. We implement continuous and iterative feedback from current and former students, ensuring that our programs and organization continue to best meet the needs of the communities we serve. TLM students across the country are taught remotely by instructors who video conference into in-prison classrooms, and TLM staff asynchronously provide support via our Student Help Desk.

With America’s incarceration rate being the world’s highest, TLM is prioritizing domestic scaling, including actively obtaining new funding and expanding to new states. Additionally, we are branching into new curriculum verticals, such as music and video production, in order to serve a broader audience of students.

If scaled globally, TLM could reduce recidivism internationally by teaching incarcerated populations in other countries the skills necessary for post-release success.

Who is the Team Lead for your solution?
Sydney Heller - Chief Program Officer
Do you qualify for and would you like to be considered for the ServiceNow US Racial Equity Prize? If you select Yes, explain how you are qualified for the prize in the additional question that appears.
  • No, I do not wish to be considered for this prize, even if ServiceNow is specifically interested in my solution/I do not qualify for this prize
More About Your Solution
About Your Team
Your Business Model & Partnerships
Partnership & Prize Funding Opportunities
Solution Team:
Sydney Heller
Sydney Heller
Chief Program Officer
Erin Palumbo
Erin Palumbo
Reentry Project Manager