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. Apply by rolling applications — interviews from we review as they arrive. Apply now →
Who we are
Closing the divide that matters now
Almost everyone in the UK is online now. That was supposed to close the digital divide, but the divide that matters today is different: it is between people who can use digital and AI tools to genuinely improve their economic position, and people who cannot.
Breakthrough exists to close that gap. We are a social enterprise working with adults from underserved communities, people carrying real structural barriers: justice system involvement, care experience, long-term unemployment, refugee backgrounds. Our mission is simple to say and hard to do: people and communities historically excluded from the digital economy gain the capability, confidence and agency to shape and benefit from an AI-enabled future.
The strongest evidence for our model is that we live it. Our CEO has lived experience of the justice system. We are the UK's first AI skills training provider to recruit directly from prison. Of the 700+ associates we have supported so far, more than 95% stay engaged with us after their programme ends. And 35% of our staff first joined Breakthrough as associates on our programmes: the people we trained now help run the organisation. We are not describing a theory. We are describing the team you would be joining.
The formal bits, briefly: Ofsted Expected Standard across all areas, Matrix Standard accredited, and a curriculum co-designed with IBM and CGI
Our partners
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'll 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.
- Lived experience of the justice system is valued at Breakthrough, from our CEO down. If that is part of your story, it may be a strength here, not a barrier.
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.
What success looks like
The bar for the first 12 months
- Deliver engaging, structured training sessions in prison education settings.
- Build associate confidence and capability with AI and digital tools.
- Maintain clear, complete progress records for every learner.
- Support associates towards genuine routes into work on release.
- Work patiently and effectively within prison security, vetting and logistics.
Working here
The case for joining now
- A small team where you get real ownership from week one. Nobody will micromanage you.
- Flexible, block-booked delivery days that fit around other commitments.
- Lived experience of the justice system is valued here, from our CEO down.
- We use AI in everything we do and will invest in you being excellent with it.
- Grow a public profile and broad skill set beyond your core delivery work.
- Be part of a team where 35% of staff started as associates on our programmes.
Location
In-person prison delivery plus remote prep
Working pattern
Freelance, part-time, rolling
Day rate
£25,000–£30,000 FTE benchmark
Deadline
Rolling applications
No CV, no cover letter.