Breaking Down Barriers from Prison to Tech with Unloop — A Case Study

Joelene Latief
Blueprint
Published in
10 min readJul 21, 2020
We built a web application to help Unloop effectively support their participants and manage their internal processes.

Unloop provides an end-to-end educational pathway into careers in software development and tech adjacent roles for people marginalized by a conviction.

A criminal record carries a stigma that far too often holds people back from their true potential, especially in the job market. Unloop works to dismantle this stigma by providing education, support, and opportunity.

Blueprint worked with Unloop to build a web application to streamline Unloop’s internal processes and participant support systems. I worked as the product designer alongside developers Calvin Chen, Christopher Grey, Erin Song, Frederick Kim, Julian Kung, and Kyle Hua, as well as product managers Divi Schmidt and Alison Dowski.

Barriers to successful re-entry:

650,000 people are released from prison each year in the US. 2 out of 3 of those people will be re-arrested within 3 years of release. The ability to find a stable, living wage job after release is a major predictor of success for someone re-entering the community.

“As we work toward systemic change and shifting culture toward a world where all people are liberated, there are people in need of immediate support whose potential and talents are overseen and ignored.

Unloop is working to ensure that our most marginalized communities who have a wealth of knowledge and skillsets to offer have access to education and job opportunities that wouldn’t otherwise be available.

— Troy Osaki, Unloop Community Engagement Specialist

This cycle affects not only those caught within it but their families and communities as well, perpetuating poverty and oppression across generations — especially among people of color.

How Unloop tackles the problem:

Unloop works very intensively with their participants. In addition to helping them find housing, social support, and all manners of other re-entry needs, they empower individuals to learn full-stack development and successfully find stable careers in tech.

“As you can imagine, there is a lot to do and a lot to keep track of. We have too many different places where we track information, and things are fragmented to say the least. “ — Misha Litchev, Director of Curriculum

As their program grows, managing the deeply individualized needs of each participant becomes increasingly difficult. Blueprint partnered with Unloop to build a software solution that enhances their onboarding for new participants and supports participant success throughout the program.

The project:

Unloop’s program starts prior to a participant’s release, with staff going into prisons and partnering with community colleges that teach technical fundamentals; during this phase, participants do not have internet access. The application that we built comes into play during the second phase of the process when participants are released from prison and re-integrating into society, while continuing their technical education and beginning their job search.

Previously, Unloop leveraged Google Suite to manage all their documents, communications, and assignments between staff and participants. Important pieces of information were difficult to keep track of, often lost in numerous folders with confusing permissions structures.

Unloop needed a central hub to decrease the administrative burden of staying on top of paperwork and the myriad of needs participants have. Working closely with Unloop leadership, we decided on building a web-based portal for both staff and participants to support organization, accountability, and transparency between parties, and ultimately encourage participant success in the long run.

A central hub to decrease administrative burden.

Without being bogged down by navigating organizational structure and communication, staff will have the opportunity to focus time and energy on moving Unloop programs forward and further supporting their participants.

Unloop’s human-centered approaches:

Designing a platform to support Unloop’s processes — not re-invent them — meant taking time to understand the intricacies of their routines and where the application would fit into them.

Through many conversations and bi-weekly meetings with Unloop staff, one key takeaway was how deeply individualized Unloop’s approach to supporting their participants is. I was consistently amazed by how available and ready to support their students each of the staff members is.

Meeting Unloop staff and participants!

MerriLynn — Student Success Manager

  • focuses on holistic re-entry success
  • has many 1:1 conversations and check-ins with participants in order to gauge overall wellness, pinpoint needs, and track progress
  • wants to understand where guidance and resources are needed while ensuring that both staff and participants are held accountable to goals

Misha — Director of Curriculum

  • focuses on technical education and career readiness
  • provides personalized support to participants entering the program at many different skill levels
  • juggles managing assignments and assessments for all students while making time for 1:1 pair-programming sessions, code-reviews, and more

In one of our calls, MerriLynn left early to go drop off paperwork and essential supplies to a participant during the height of the pandemic. In another, Misha told us how he had stayed up late the night before helping a student debug a client project they were coding for contract work.

This personalized support perpetuates through Unloop’s approach to all parts of the program, from onboarding participants, to technical assessments, to measuring participant success and growth, and it heavily influenced my approach to designing the app.

I wanted to make sure features are designed not to replace the in-person interactions between staff and participants, but enhance them by serving as a platform that brings awareness to areas that staff can meaningfully impact, whether in re-entry needs, technical support, or anything in between.

Keeping track of all these individual needs of participants means having a high degree of communication and transparency, so that information doesn’t fall between the cracks, and staff resources and energy can be allocated effectively.

What we built:

Unloop aims to give participants a sense of consistency and “home” in an otherwise difficult transitionary period in their life releasing from prison and returning to their communities.

“Staff have been there for me whenever I needed strength, encouragement, or assistance navigating the complexities of freedom in what has been the most difficult journey of my life. I know that every staff member genuinely believes in what they are doing and are personally invested in the success of every participant.”

Travis, Unloop Graduate

The app aims to support this mission by offering:

  • a streamlined onboarding process for participants transitioning into the program
  • a central hub for information and transparent communication between staff and students
A one-stop-shop for all of Unloop’s administrative needs and participant management.

1. Streamlining onboarding

Unloop’s onboarding process involves staff assessing the immediate needs of participants, such as a stable living environment, mental health resources, transportation, WiFi, and other basic necessities, as well as managing large amounts of paperwork that comes with re-entry, such as judgement and sentencing documents and other agreements.

Feature: paperwork and intake forms

  • Makes it easy to manage numerous documents and intake forms for each participant.
  • Helps consolidate information for grant applications
  • Ensures that staff stays aligned on the unique backgrounds of each participant entering the program.

2. Simplifying communication

Assignments for Unloop cover a wide range of categories such as:

  • health (doctor, dentist, or therapy appointments)
  • finances (budgeting and financial wellness classes)
  • community engagement (networking events or social get-togethers)
  • technical (coding assignments and projects)
  • career (resume reviews and job applications)

Previously, all of these were managed through email, text, and Google Drive, requiring substantial manual effort to assign and track. Additionally, more complex operations like reusing past assignments, assigning recurring ones, or curating groups to automatically assign multiple assignments to were complicated or entirely inaccessible.

Feature: Bulk Assignment

  • Allows staff to manage complex communications while maintaining Unloop’s organization-wide assignments framework; staff can efficiently communicate information regarding resources, opportunities, and curriculum with large, diverse groups of students.
  • Tracking the completion of assignments offers indicators of participant engagement and success throughout the program.

3. Centralizing information

Staff notes store a diverse amount of information such as housing contacts, job search updates, observations on a participant’s mental health, and even notes of support and encouragement. All of these pieces of information were previously stored in multiple Google docs, with some shared with participants and some meant to be internally facing only.

Feature: Case-notes

  • Centralizes staff notes and make communications more transparent between staff and participants; staff can easily toggle visibility and permissions for case-notes for increased organization-wide transparency.
  • Facilitates knowledge transfer between staff members and increased awareness of individual participant needs.

4. Making progress trackable

As students progress through the program, they are given assessments with questions centered around core technical concepts that are taught, such as React.js, database fundamentals, and technical problem-solving. These tests are given to help pinpoint areas for growth, match participants to career opportunities, and measure progress in technical skills as they move through the curriculum.

Feature: Studio Assessments and Dashboard

  • Allows staff to find participants more tailored opportunities for skills they excel at.
  • Gives concrete measures of progress for staff to see improvement through the program, and improve support in areas that need it.

Results and looking forward:

In Fall 2019, my team and I designed and launched our MVP for the app with the onboarding and case-notes features. Once Unloop started using the application in January 2020, we gained even more valuable feedback that we iterated on throughout the spring while building the remaining features.

Early user feedback session with Misha and Troy

For example, improvements such as having formatted fields in our intake forms for more standardized data recording and improving copy to better fit their organizational language led to better usability and ultimately a more seamless transition for staff onboarding onto the platform.

We have officially handed off the application to Unloop, and they are even gearing up to have participants looking for practical web development experience to continue developing and improving the platform in the future!

Design Reflections:

Designing for Unloop gave me so much insight into building for unfamiliar contexts, collaborating effectively with developers, and keeping users at the forefront of every design decision.

Some key takeaways:

Understanding why your end-user wants a feature is key to tackling the root of the problem rather than its effects. Originally, Unloop came to Blueprint with a project proposal and features in mind. My role as designer, alongside my project leader, was to work with Unloop staff to understand how what we were building would accelerate the organization’s efficiency, before jumping into development.

Unloop’s processes are still evolving and improving as the program matures and develops; as a result, while designing and building this application, the best thing that we could do to design for longevity was ask good questions that lead to stories about process and test along the way, in real scenarios. As someone external to their organization, asking the right questions always helped clarify and inform my design decisions, or even occasionally led to them reflecting on their own processes and how they could be improved in the future as they continually strive to better support their participants.

Learning to balance tradeoffs between value add and development effort is crucial. Working within a limited time frame forced us to be very intentional about what we spent our development time on, which I believe was ultimately beneficial to the final product.

Collaborating closely with a team of developers to build this platform, as well as jumping into code to build some features, allowed me to better understand how each feature was impacting our project timelines and make more informed decisions about how to approach and prioritize designs. On a related note, having established guidelines for designer/developer collaboration, such as having developers onboarded onto Figma, our design software, and know how to effectively translate designs to code, helped us iterate quickly and stay on track.

Final thoughts:

I have so much respect for the work that the Unloop team is doing, and I can’t wait to see how the organization grows and impacts people’s lives in the future. Special thanks to Troy, Misha, MerriLynn, Michael, and the rest of the Unloop team for the dedication and time they spent with my team and I to help us understand their work and goals for the future!

If you are able, please consider supporting Unloop during these times!

COVID-19 has exacerbated many of the difficulties of returning from prison. As Unloop responds to their participants’ needs at each level of service, their needs are increasing: they are expecting a 30% increase in participants being released from prison as correctional facilities attempt to limit the spread of COVID-19. Your donation will support Unloop in raising funds for items such as hygiene products, sheets and pillows, laptops, grocery funds, and rent assistance.

photos of some lovely Blueprint developers, designers, and project leaders who I learned so much from while building this project

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