Steve Shickles
Founding Alumni Member
Chief IT Engineer
Areas of Focus
Service and Purpose
Steve Shickles became a member of the Prison Professors community while he was in the midst of judicial proceedings. He faced wire fraud charges, a white-collar offense, and chose to respond proactively rather than retreat into denial or passivity.
Before sentencing, Steve made deliberate use of the resources available through Prison Professors.
He developed a clear personal narrative that acknowledged responsibility and demonstrated growth.
He organized a campaign for character reference letters.
He worked methodically to build a comprehensive mitigation strategy.
Steve’s preparation before sentencing reflected discipline, foresight, and a willingness to confront difficult realities directly.
A federal judge sentenced Steve to serve a 60-month term of imprisonment. Despite the length of that sentence, Steve continued applying the same principles that guided his preparation before sentencing. Through consistent effort, disciplined behavior, and documented progress while incarcerated, the Bureau of Prisons authorized his transfer to a halfway house after he served approximately 19 months.
Following his release, Steve remained deeply engaged with Prison Professors. He began volunteering his time and expertise, contributing to the growth and stability of the organization. Today, he serves as our Chief IT Engineer, where he plays a critical role in building and maintaining the systems that support thousands of people documenting their preparation for release.
I invited Steve to join the Prison Professors Faculty because of his exceptional technical skill, his commitment to service, and his ability to translate personal accountability into practical contribution. His story demonstrates a core principle of this platform:
Regardless of the mistakes people have made, at any point they can begin making better decisions, recalibrate their direction, restore confidence, and begin writing the next chapter of their life.
I am grateful to have Steve on our team and to count him among the faculty members who help others turn preparation into opportunity.
Foundational Contribution
Steve’s foundational contribution to Prison Professors is rooted in his commitment to building systems that expand access, improve usability, and remove barriers to participation.
Working full time with the organization, Steve leads efforts to improve the user experience across the Prison Professors platform. He focuses on making the website more intuitive, reliable, and accessible, ensuring that people at every stage of the justice process can understand how to document their preparation and engage meaningfully with the tools we provide.
Steve also serves as a trusted guide in the responsible use of technology and artificial intelligence. He advises on how emerging tools can be applied to help more people build credible narratives, organize their work, and communicate their progress clearly. His guidance helps ensure that technology strengthens accountability and preparation rather than replacing personal effort.
A central principle of Steve’s work is accessibility. He is deeply committed to ensuring that people can learn and participate regardless of their ability to pay. Through thoughtful design and technical decision-making, he helps the organization deliver educational resources at scale while preserving the integrity of the Prison Professors mission.
Steve’s contribution extends beyond code and infrastructure. By aligning technology with values, he helps transform preparation into opportunity for people who are willing to show their commitment to pursuing excellence.
Impact Narrative
Steve’s impact on Prison Professors is reflected in the systems he has built to make progress visible, measurable, and transparent.
He engineered a real-time dashboard that allows stakeholders to see the impact of the Prison Professors platform as it unfolds. Through this system, we can track participation, engagement, and documented effort across the community, providing clear, up-to-date insight into how people are using their time to prepare for success upon release.
This capability has strengthened our ability to communicate with policymakers, institutional partners, donors, and community leaders. Instead of relying on anecdotes or summaries, we can now demonstrate outcomes with data that reflects real activity, real consistency, and real growth. The dashboard turns individual effort into collective evidence.
By making impact visible in real time, Steve has helped elevate the credibility of the organization and the people we serve. His work ensures that preparation is not only encouraged but also verifiable, reinforcing the Prison Professors principle that trust is built through documentation and sustained action.
Post-Release Service
Following his release, Steve continued his commitment to preparation and service by joining the Prison Professors leadership team. In this role, he helps design and build the systems that allow the organization to serve people at scale while remaining accessible to anyone who wants to learn.
Steve works closely with the team to ensure that Prison Professors can offer free educational resources to individuals regardless of financial circumstance. His focus is on creating infrastructure that removes friction, simplifies participation, and makes it easier for people to take responsibility for their own preparation.
Through his work, Steve helps expand the organization’s reach and effectiveness. He supports systems that teach people how to help themselves by documenting effort, building structure, and making informed decisions about their future. His post-release service reflects a long-term commitment to empowering others with tools, clarity, and opportunity rather than dependency.
Steve’s leadership demonstrates how technical skill, when aligned with values, can extend access, strengthen accountability, and support meaningful transformation for people seeking a second chance.
Teaching Focus
Steve’s teaching focus centers on helping our team use technology and systems effectively to serve people at scale. His instruction is practical, iterative, and grounded in real-world application.
Steve works closely with me and with members of the Prison Professors team to explain how technology, automation, and artificial intelligence can be used responsibly to support thousands of people who rely on our free services. He teaches us how to design systems that are intuitive, efficient, and aligned with our mission, so that individuals can access guidance, document their work, and learn how to advocate for themselves.
Rather than teaching technology for its own sake, Steve focuses on how systems can empower people to take ownership of their preparation. He helps the team understand how to simplify workflows, improve communication, and reduce barriers so that more individuals can engage meaningfully with the platform.
Through this work, Steve plays a critical teaching role behind the scenes. His guidance enables Prison Professors to scale without losing clarity, accessibility, or integrity, ensuring that education and opportunity remain available to anyone who is willing to do the work.