When Jacob Hill talks about what a person with a criminal record looks like, he gestures to himself. “You think Shawshank Redemption or Prison Break,” he says, “but actually it can just be a normal person.”
At 19, Hill was running a camping business and had raised £330,000 in investment. When the venture failed, debts spiraled. In a moment of panic, he decided to sell drugs at a festival to pay them off.
The story quickly reached home: his mother was a police officer, and his father a retired drugs investigator. Their son’s fall from grace made headlines. He was sentenced to 28 months in prison.
“My parents visited me every week,” he says. “That was privilege. Many people don’t have that. Some can’t even open a bank account when they leave.”
Hill’s first job inside was sewing boxer shorts: 200 pairs a day. His cellmate, Ralph, known as “Mr. Big,” acted as boxer quality control. “He checked every single pair,” Hill says.
“[Mr. Big] had real skill and pride in his work. People in prison come from every walk of life. A quarter of adults in the UK have a criminal conviction — there’s talent there.”
After his release, Hill founded Offploy, a social enterprise that mentors people with convictions and helps them into work. Its motto is “prison to purpose.”
According to a 2024 analysis by the UK Ministry of Justice, support from Offploy decreased the number of proven reoffenses among former inmates during a one-year period compared with a control group. Its success stands as a powerful case study in what modern rehabilitation can achieve — and how technology can enable it.
The digital leap
When Offploy began, it faced the same administrative inertia that still holds much of the justice sector back. “The prison service are terrified of digital setups,” Hill says. “They love a wet paper signature.”
He recalls that moving from paperwork to a cloud-based CRM was an unusual move for the sector. But the real transformation came later, with the adoption of Conga, a suite of workflow automation tools built on Salesforce.
Offploy now uses three Conga products:
- Conga Grid, which provides a data dashboard.
- Conga Composer, to collate information about an individual’s journey through multiple systems into one document.
- Conga Sign, to enable digital signatures on information-sharing agreements between Offploy, commissioners and the probation service.
The result is a single source of truth. “Probation want information by secure email; commissioners want it in Excel — Conga allows us to do it all in one system,” Hill says.
Tangible outcomes
The measurable impact has seen Offploy reduce paperwork by 80%, scale candidate support by 300% and cut administration time from 16 hours per person to just 30 minutes. The efficiencies save the equivalent of £60,000 in staffing costs annually, according to Hill.
More importantly, the automation is tangibly affecting the lives of its participants. Judges can now sign people directly into community referral programs, with court, probation and police accepting the automatically generated documentation as official. “That process alone saw 20 people go through our program instead of prison,” Hill says.
Program participants using Offploy’s system can now see their progress in one place: goals, achievements, signatures and case notes.
“Conga lets us treat people like customers,” Hill explains. “That’s what keeps them engaged — and it keeps commissioners renewing our contracts.”
From digital paperwork to digital empathy
The pandemic was another turning point. “When it struck, we had a societal shift,” Hill says. “We realized we needed technology that could help us stay connected, even remotely.”
Offploy is now exploring artificial intelligence to take that connection further. Hill envisions AI tools that transcribe case notes from recorded calls, or even voice agents built from thousands of hours of mentoring sessions.
“Imagine finishing a call and the case notes are written automatically,” he says. “Or imagine a 24/7 support line, where people know they’re talking to an AI — but it listens, records goals, updates probation officers.”
Scaling purpose
Offploy’s technological backbone also powers its Disclosure Calculator, an online tool that helps people understand when they no longer need to declare past convictions to employers, landlords or banks.
“Four years after prison, I still had to disclose everything,” says Hill. “If you don’t, it’s another offense. We built the calculator so people can see clearly when that ends.”
Hill believes Offploy’s mix of empathy, technology and efficiency is what sets it apart.
“Where there are people, there are criminals,” he says bluntly. “Our IP is our nine-step program, but we give it away for free. The real IP is the technology behind it.”
Hill plans to scale Offploy five-fold by 2028, expanding its model and disclosure tools across Europe. “France takes a similar approach to the UK. Australia has different rules per region,” he says. “We can adapt the calculator for each.”
The goal is simple: to make re-entry into society as seamless as any other customer experience. “The justice sector is always 10 or 15 years behind,” Hill says. “But with the right data, automation and empathy, we can catch up — and make society safer in the process.”
