Prison Delivery Executive (Freelance)

Deliver AI skills that open doors on release Facilitate AI and digital skills training inside prisons. Help people build capability, confidence and a genuine route into work on release. In-person prison delivery plus remote prep

Freelance, part-time, rolling applications

How to apply Rolling applications: we review as they arrive. Note that prison security vetting takes around 8 weeks, so apply early.

The role Prison Delivery Executive (Freelance) We deliver AI and digital skills training inside prisons with partners including BT, Syscon and TPX. You will facilitate sessions in the prison environment, helping associates build skills, confidence and a genuine route into work on release. This is not a standard training job. It is facilitation inside a complex, high-integrity environment where patience, adaptability and genuine respect for every learner matter more than polished slides. Deliver structured sessions Facilitate engaging AI and digital skills sessions in prison education settings, working within the constraints that environment brings. Track progress Monitor associate progress and keep clear, complete records for every learner. Work flexibly Sessions are booked in blocks and a delivery day is a full day on site, with remote prep in between. Build confidence Help associates develop skills, confidence and a genuine route into work on release. Teach without jargon Be confident with AI and digital tools and explain them in ways that land with learners at every level. Lived experience valued Lived experience of the justice system is valued at Breakthrough, from our CEO down. It may be a strength here, not a barrier. Beyond your day job Get involved in the wider mission Breakthrough is a small, fast-moving team. Whatever your role, you will also get involved in things like appearing in our social media and video content, contributing to reporting and impact stories, and supporting recruitment and events. If you want a narrowly defined job, this is not it. If you want to grow a public profile and a broad skill set alongside your core work, you will love it here. You will thrive here if You are a calm, adaptable facilitator who treats every learner as capable, whatever their past. You are patient with uncertainty: vetting, security and prison logistics reward people who plan ahead. You are confident with AI and digital tools and can teach them without jargon. Practical details Prison security vetting is required and takes around 8 weeks; we will support you through it. An enhanced DBS check is also required.