Peter Chatwell
Director and CEO
About Pilot 2 Work
A Kent-based social enterprise born from a belief that no young person should face their future alone. Our story is one of passion, purpose, and the transformative power of community.
Our Founder: Peter Chatwell
Peter Chatwell founded Pilot 2 Work CIC in 2023 with a clear mandate: use AI to close the employment gap for young people in Kent and Medway who are most at risk of being left behind. Before founding P2W, Peter spent over a decade working in community development roles across Medway — including as a programme coordinator at a Medway-based youth offending prevention service and as a volunteer mentor with a Kent-wide NEET reduction initiative — where he repeatedly encountered the same structural problem: talented, motivated young people failing to reach employment not because of ability, but because of a system not built for them.
That frustration led to Pilot 2 Work. Rather than replicating existing job-board models, Peter set out to build something genuinely different — an AI-powered coaching platform that combines personalised career guidance, neurodiversity-informed support, and justice-aware employment pathways under one roof, as a registered Community Interest Company with 100% of profits legally required to be reinvested into the community it serves.
Based in Chatham, Kent, Peter leads Pilot 2 Work with a commitment to measurable outcomes — not just engagement statistics. His benchmark is simple: did a young person get a job, an apprenticeship, or a clear pathway forward?
What Drives Us
Our Mission & Values
Our mission is simple: to ensure no young person is left behind when taking their first steps into the world of work. These are the values that guide every programme, every coaching session, and every partnership we build.
Inclusive
Every young person deserves a fair chance, regardless of background, ability, learning style, or circumstance. We design everything with inclusion at its core.
Innovative
We harness the power of AI and emerging technology to create personalised, effective employability support that scales without losing the human touch.
Community-First
Every decision we make puts the young people of Kent, Medway, and beyond at the heart of our work. We are rooted in our community and proud of it.
Transparent
We are open about who we are, what we do, how we use data, and how we invest our resources. As a CIC, accountability is not optional — it is our foundation.
Recognised & Accredited
Our Accreditations
Meet the Team
A dedicated group of professionals united by a shared mission to empower young people.
Piers Bennett
AI Policy and Compliance Officer
Oscar Stollery
AI Engineer
Matt Ledger
AI Engineer
Jacob Roberts
AI Engineer
Damien Di Falco
AI Engineer
Lucas Reddington
AI Engineer
Apprentice Spotlight
Oscar's Story
We are absolutely thrilled to shine a spotlight on Oscar, our dedicated AI Apprentice Engineer, and celebrate the incredible progress he's made with Pilot 2 Work CIC!
“Choosing this apprenticeship route was driven by my desire for a meaningful combination of hands-on work and formal learning. A major technical achievement has been developing the skill to create and maintain a database, a capability I immediately applied when I engineered the code to migrate our SQLite database files to an Amazon Web Services PostgreSQL server. My understanding of collaboration also grew significantly, primarily through utilising GitHub in project teamwork. While I found mastering time management the most challenging professional behaviour, implementing the MS Teams planner helped me significantly improve, and using the Eddy AI tool has had the biggest positive impact on my overall performance. My greatest obstacle was tackling the apprenticeship portfolio, which I successfully overcame thanks to regular meetings and consistent feedback from my mentor. With my confidence level now at a 4 out of 5, I've already seen a positive impact by speeding up progress for the team. Moving forward, my ambition is to complete the program and stick with Pilot Generative AI, but with a sharper focus on the AI side of the technology. Ultimately, this apprenticeship has given me the perfect chance to learn while working on something I am deeply interested in: AI.”
Oscar
AI Apprentice Engineer, Pilot 2 Work CIC