Power of a resolution: How FreeWorld uses Zendesk to create second chances

FreeWorld Founder and Executive Director Jason Wang carries with him a mission that is both deeply personal and unapologetically ambitious: to end mass incarceration in our lifetime by creating clear, fast pathways to living-wage careers. Jason knows the stakes. At 15, he made some terrible decisions that led to a 12-year sentence in a maximum-security prison. While he was ultimately released early, earned a full scholarship and two master’s degrees, he was still unable to find employment due to his record.

His experience wasn’t an exception, but one felt acutely by the tens of millions of Americans with criminal records. Out of that experience, FreeWorld emerged.

A Zendesk Tech for Good grantee, FreeWorld’s mission is simple: to provide every returning citizen with equitable access to living-wage careers in multiple career fields. Today in trucking, tomorrow across multiple pathways.

How quick resolutions become second chances

In the customer service space, a “resolution” might mean a complex return is processed or a shipping address is corrected. However, as Jason points out, for FreeWorld, a resolution is much more than just an endpoint.

“When somebody comes out of prison, there’s no time to waste. Just imagine somebody who’s been incarcerated for 10 years. They don’t know the latest apps on a mobile phone. The things that they learned to be successful 10 years ago are not the same things that will allow them to be successful today,” said Wang. “For people coming out of the incarceration system, speed is important. Speed to get services, speed to reintegrate back into society, speed to be able to get their education that then would qualify them for a job. And so, that’s how Zendesk helps us.”

FreeWorld’s students, known as “Free Agents”, arrive with a wide range of needs: a ride to class, clarity on a training concept, help navigating parole, or assistance applying for important documentation. For FreeWorld, resolving these issues is critical and can mean the difference.

Resolution in action

FreeWorld sees the power of a resolution every day.

A recent example: a Free Agent had been searching for work since March 2024. His conviction was recent, and rejections piled up as soon as employers saw his background check. He was ready to quit trucking altogether and go back to warehouse work.

Instead of letting him give up, FreeWorld’s career services team, or Coaches, kept showing up. Then the breakthrough. A fellow Free Agent with seniority at a trucking company shared an opening. FreeWorld made the connection, and everything changed. He landed a job earning $91,000 a year.

Arming FreeWorld’s skilled and empathetic success Coaches with Zendesk’s AI-powered resolution platform allowed a resolution to not only restore confidence for the end-user, but deliver a life-changing wage, and stability for a family.

Support like this is the reason that 98% of FreeWorld’s graduates do not return to prison upon completion of the program.

From scattered to streamlined: centralizing AI-powered support with Zendesk

Before Zendesk, FreeWorld’s support model looked like a lot of scrappy startups. Silo’d channels like voice, emails, texts, and internal messaging, all trying to wrangle thousands of nuanced requests each month. There was limited visibility into who was helping whom, no reliable way to prioritize responses, and a constant risk of duplication or missing requests altogether. Today, Zendesk is FreeWorld’s communications backbone.

“We would have success coaches that would be supporting an individual, but somebody else was also supporting an individual, and there’s no visibility between the two. Zendesk helps us solve that problem across the board,” said Wang. “It’s effectively is our main communication tool for literally everything, whether it’s inbound emails, or working with our free agents, or working with government partners, it all gets routed through the Zendesk platform.”

The result is strong record-keeping, clear accountability, and faster time-to-resolution. To amplify impact, FreeWorld integrated Zendesk AI Agents directly into their Free Agent student portal. Support is now just a click away, right where Free Agents are already working.

The outcomes speak for themselves: transfers to human coaches dropped from 35% to 28% and because of that, the team saves 8 hours of staff time every month.

Those hours add up over a year, unlocking more time for what humans do best: high-empathy, high-stakes coaching on issues like addiction, family dynamics, or navigating complicated power structures outside of prison. Moreover, Free Agents get shorter wait times and active support at odd hours. Vital for people juggling work, classes, and reentry.

“For a lot of our Free Agents, their challenges aren’t because they don’t have drive or motivation. We find that our students are some of the most motivated people out there. Oftentimes, the real challenge is lack of access to resources, especially, resources that are understandable,” said Wang. “That’s why FreeWorld built our Zendesk Help Center as a true self-service engine, with materials designed by people with lived experience who know precisely what questions arise and when.”

As FreeWorld grows into new states and partnerships, the strength of its core operations, powered by tools like Zendesk, ensures that support scales without losing the human touch.

Their long-term vision remains audacious: make reentry as easy as the click of a button.

That’s the power of a resolution. And with FreeWorld and Zendesk working together, second chances aren’t just possible, they’re happening everyday.