When It Clicked – “A Better Way For Prisons To Leverage AI”
Podcast: When It Clicked (Lemonada Media)
Host: Ana Zamora
Guest: Clementine Jacoby (CEO & Co-founder, Recidiviz)
Date: December 17, 2025
Episode Overview
This episode explores how technology—and specifically AI and better data systems—can drive real, positive reform in the American criminal justice system. Host Ana Zamora interviews Clementine Jacoby, CEO of the nonprofit Recidiviz, about modernizing prison data infrastructure, breaking cycles of recidivism, and why centering humanity and dignity is crucial to change. The discussion moves from Jacoby’s personal motivation to specific examples of how Recidiviz’s tools are being used to help tens of thousands of people return home, influence policy, and support incarcerated individuals’ reentry into society.
Key Discussion Points & Insights
1. Origins and Motivation
Personal Impact and Systemic Realization
- Clementine describes her upbringing: mom in addiction medicine, dad a political scientist, and how seeing her uncle get a harsh prison sentence for a nonviolent teenage crime exposed the flaws and arbitrariness of the justice system.
“My family thought for sure he would get, like, I don’t know, community service or a fine or something. But he got a 10 year prison sentence... a third of his life to that point, his whole adult life in prison. And... a few months later, ended up going back in.” (03:56 - 05:10, Clementine Jacoby)
- Realized how little control families have and how systemic cycles are hard to break.
“That was when I started studying the system in earnest, because I realized that he was caught in a cycle that even to this day, my family has proved unable to pull him out of.” (05:10, Clementine Jacoby)
Firsthand Encounter with Systemic Arbitrary Nature
- Her family’s experience highlighted the arbitrary nature of sentencing and the justice system’s unpredictability.
“I remember really, it all of the sudden feeling much more arbitrary than it had felt before. And I think that that is a realization that so many Americans go through.” (06:02, Clementine Jacoby)
2. Founding and Evolution of Recidiviz
From Side Project to Nonprofit Startup
- Jacoby and friends started by aggregating criminal justice data. What started as volunteer work at Google gained traction after a corrections director in North Dakota noticed them.
- Visiting North Dakota prisons revealed the problem was less about transparency and more about “modernization”—the data systems were so fragmented that staff couldn’t track people’s progress or decisions effectively.
“We would enter a state, we would connect these databases, and when we did that, we could see from the math that many, many people were already eligible to be released...” (10:18, Clementine Jacoby)
Recidiviz’s Mission and Model
- Recidiviz partners directly with state corrections departments to connect fragmented databases, clean up data, and deploy AI tools for better decision making.
3. The Scale and Nature of the Data Problem in Corrections
Overstaying Due to Data Fragmentation
- Approximately 250,000 people are incarcerated or under supervision past their release eligibility due to data problems.
“So these are folks that have done their time, quote unquote, but they're still either in prison or they're under some sort of supervision.” (09:20, Ana Zamora) “Every time you pass... [a] policy... earned time for something, it goes in a different database, and none of them talk to each other.” (10:18, Clementine Jacoby)
- Many sentences come with possibilities for reductions through programming or good behavior; disconnected databases mean earned credits are missed.
Consequences for Individuals and the System
- The failure to integrate data keeps people incarcerated unnecessarily, exacerbates overcrowding, and overburdens probation/parole officers.
- Better data and automation can safely reduce the population under correctional control and free up staff to provide more meaningful support.
4. Technology’s Transformative Role
The Day in the Life Before and After Recidiviz
- Pre-Recidiviz: Staff overwhelmed by paperwork, security concerns, and manual processes, leading to a purely custodial approach.
- With Recidiviz: Automated paperwork, eligibility tracking, and individualized roadmaps to reentry allow both staff and incarcerated people to know where they stand and what’s next.
“The day that someone enters prison, everyone who's working with them can see their shortest and most rehabilitative path to freedom.” (14:24, Clementine Jacoby)
- Automates notifications and paperwork, streamlining processes that used to be bottlenecks (e.g., early termination from probation).
- By reducing case loads for staff, more time is available for actual support (e.g., helping maintain housing, employment).
Memorable Quote on Impact
“That flywheel is important, because you’re not only helping the people that were already ready to be released ... you’re also helping everyone who needed a little bit more support from that case manager that was otherwise overwhelmed.” (17:46, Clementine Jacoby)
5. Impact on Policy and Reforms
Influencing Administrative & Legislative Policies
- Improved data helps identify and resolve bottlenecks, both legislative and administrative.
- Example: Arizona shifted ~39% of people on supervision to remote check-ins, improving stability and outcomes (and saving resources) by leveraging Recidiviz’s analytics for policy calibration.
“They designed this new level in house and then they moved about 39% of people to it. And they used our analysis to calibrate that policy using their own data and then one of our tools to make sure that they were moving people consistently...” (19:21, Clementine Jacoby)
6. AI and Generative Tools for Personalized Reentry
Scaling Tailored Support with AI
- Traditional staffing ratios (one case manager per 300+) make individual support impossible; AI-powered case planning assistant now used in Utah and other states.
- LLM-based chatbot interviews incarcerated people months before release, producing personalized action plans aligned with individual motivations (housing, employment, reuniting with family).
Real, Human Motivation Centered
- Example: An incarcerated person’s desire to reunite with his children after his wife’s death became the centerpiece of his reentry plan.
“As I was reading the transcript of the conversation and looking at the action plan that it built, that driving force was in there, right at the top...” (24:09, Clementine Jacoby)
- AI allowed for deeper, more personal engagement than the “rote and scripted” human process.
“We know reentry doesn’t work, right? Like, 8 in 10 people who leave prison one day come back. And so this is such a huge problem that you have to try everything that you can try.” (26:48, Clementine Jacoby)
7. Direct Access and Empowerment for Incarcerated People
Breaking Information Asymmetry
- New tech (tablets) makes it possible for incarcerated individuals and staff to share the same “roadmap.”
- Texts and notifications help people out on probation/parole avoid missing appointments or requirements—small changes that prevent reincarceration.
“We recently ran a survey with over 10,000 people in prison and found that half of them didn’t know their release date... And so that roadmap to reentry... now you can sort of break the information asymmetry. And the staff and the people in prison can be looking at the same thing.” (30:36, Clementine Jacoby)
8. Are We at a Tipping Point?
- Zamora asks whether the work has reached a “tipping point” for this to become the norm in US corrections.
- Jacoby is both optimistic and realistic: the sector is far from full adoption, but culture among leaders is changing as they witness real results and accountability through data.
“80% of the time I spend in the first world where I think, like, ugh, we're just getting started... And then maybe 20% of the time I like, step back and watch how people are using these tools... and I think like, man, that's pretty cool.” (33:08, Clementine Jacoby)
Notable Quotes & Memorable Moments
-
On why the system feels arbitrary:
“I remember really, it all of the sudden feeling much more arbitrary than it had felt before. And I think that that is a realization that so many Americans go through.”
– Clementine Jacoby, 06:02 -
On the power of data-driven reform:
“The day that someone enters prison, everyone who's working with them can see their shortest and most rehabilitative path to freedom.”
– Clementine Jacoby, 14:24 -
AI’s impact on hope and motivation:
“I really do think that motivation, efficacy, hope on the side of the person who is incarcerated… that hope and delivering that hope does lead to different outcomes.”
– Clementine Jacoby, 30:01 -
On seeing change across states:
“You’re realizing that, like, I don’t know, when we started six years ago, I don’t think anyone would have even been comfortable launching these tools for people directly in prison. And you think like, man, I guess this is the tipping point.”
– Clementine Jacoby, 33:22
Timestamps for Key Segments
- 03:56 – 07:20 — Clementine’s personal motivation & family experience with criminal justice
- 07:20 – 10:18 — Starting Recidiviz; shifting from volunteer work to building tech for corrections
- 10:18 – 14:24 — Explaining the scale of the data problem (over-incarceration due to poor systems)
- 14:24 – 18:02 — Pre/Post Recidiviz: staff processes, benefits of automation and individualized roadmaps
- 19:21 – 21:01 — How data tools drive policy reform (Arizona’s remote supervision example)
- 22:05 – 27:32 — AI for tailored case management, the first 72 hours after release, real-life impact stories
- 30:36 – 32:17 — Empowering individuals with direct access (tablets, notifications, shared roadmaps)
- 33:08 – 35:40 — Are we at a tipping point? Reflections on progress and remaining challenges
Summary
This episode of When It Clicked provides an in-depth, human-centered look at how AI and data can dramatically improve outcomes in the U.S. justice system. Clementine Jacoby passionately shares her journey and the intentional ways Recidiviz uses technology to bridge gaps, empower people, and help government do better—emphasizing that modernizing prisons isn’t just about efficiency, but about rebuilding trust, hope, and real opportunity for those inside and outside the system. Ana Zamora’s probing questions keep the conversation grounded in its real-world, human impact, driving home the episode’s central theme: reform is possible, and it’s already happening.