Oscar's Story: From Apprentice to Team Member
Oscar Stollery joined Pilot 2 Work as a digital apprentice at a point when he was, in his own words, "interested in AI but not sure how to get a foothold in it." He had the curiosity and the motivation. What he needed was the combination of real work experience and formal structured learning that an apprenticeship provides — and that most entry-level tech hiring processes are not designed to accommodate.
Two years later, Oscar is a full member of the engineering team, has migrated our entire database infrastructure from SQLite to AWS PostgreSQL, and has been rated in the top cohort of his apprenticeship programme by his training provider.
The apprenticeship journey
Oscar is candid about what was hard. "Mastering time management was the most challenging professional behaviour for me. I knew how to do the technical work — it was the project organisation and the portfolio documentation that I found difficult at first." His solution was practical and systematic: adopting MS Teams Planner for task tracking, establishing regular check-ins with his mentor, and building a habit of documenting work as he went rather than retrospectively.
On the technical side, Oscar points to two milestones that stand out. The first was developing the skill to design and maintain a relational database — "a capability I immediately applied when I engineered the migration of our SQLite database files to an Amazon Web Services PostgreSQL server." The second was developing real fluency with version control and collaborative engineering through GitHub, moving from using it primarily as a backup tool to genuinely understanding branching, code review, and pull request workflows.
The Eddy AI tool — the platform Oscar was helping to build while simultaneously learning his craft — had what he describes as "the biggest positive impact on my overall performance." Using the tool he was developing to manage his own work gave him a perspective on its design that no external user testing could replicate.
What comes next
"My ambition is to complete the programme and stick with Pilot Generative AI, but with a sharper focus on the AI side of the technology," Oscar says. "This apprenticeship has given me the perfect chance to learn while working on something I am deeply interested in."
Oscar's story is a clear illustration of why Pilot 2 Work exists. The traditional route into technology careers — a computer science degree, followed by a graduate programme — is not the only route. For young people who learn by doing, who need to earn while they learn, or who simply find the academic path a poor fit for how they think, apprenticeships offer a genuine and increasingly respected alternative.
We are proud to support young people like Oscar — and we are proud that he chose to stay with us.
If you are interested in exploring apprenticeship routes in technology, or if you are an employer considering taking on an apprentice, get in touch.