Trainee System Administrator 2026

Oleeo is seeking an entry-level Trainee System Administrator who is an IT Support professional, an apprentice, or a self-taught technology enthusiast looking to move into Systems Administration and Infrastructure Engineering. This is an incredible opportunity if you want to shift from tech support to designing, building, and automating resilient environments with outstanding mentorship in an entrepreneurial culture. We will ensure you receive quality, structured training on your journey to becoming an all-round professional System Administrator.

It's a very hands-on role where you will provide immediate operational relief to our infrastructure team and make a real impact early on. Your responsibilities will grow systematically as you progress through our training programme. You will ensure our internal environments and platforms run smoothly to support next-generation online Software-as-a-Service (SaaS) products for recruitment.

Using our action-oriented training methodology, your progression will focus on executing real-world technical workflows to achieve measurable professional development goals. From the first day of your training, you will be part of a wider technical operations team, working closely with system administrators, developers and product management. Your exposure and strategic responsibilities will grow alongside your technical skills.

This is a hybrid role based in Wimbledon, with expectation to be in our office in Wimbledon in South London once a week for IT Support tasks.

• Must have some demonstrable experience in IT Support, whether gained during formal employment, apprenticeships, or personal time
• A proven track record or strong background in hands-on IT troubleshooting
• Curiosity and analytical problem-solving skills
• Eager to learn
• Demonstrable critical thinking
• Outstanding attention to detail
• Evidence of problem-solving and the ability to 'grok' things
• Able to work in the UK without any restrictions. Security Clearance required in this role which means 5 year UK residency history is required.

Oleeo means a diverse collection of things that together, make something beautiful. That’s how we see ourselves; a diverse team of technology and talent acquisition professionals who’ve come together to achieve something beautiful. We are proud to be a team of individuals that collectively deliver powerful data-driven automation, for fast, efficient, engaging and inclusive recruitment.

Our purpose and passion is to support organisations, to engage and hire great, diverse talent, quickly, efficiently and without bias. As pioneers in recruitment software, our solutions are built to accelerate and improve the entire recruiting process, creating a more meaningful, engaging and transparent experience for candidates and enabling recruiters to be the very best they can be.

Established for over 20 years with offices in London, New York and a presence in Asia, we are proud to list some of the world’s most talented organisations like The NHS, Morgan Stanley, The Metropolitan Police, Amazon and Bank of America among our customers.

We foster a terrific, diverse, flexible culture where people are empowered to work in ways that suit them best. Our authentic environment is the primary reason our colleagues love being part of Oleeo. Our values are centred around people, our colleagues and customers.

The technical team is about 30 people in total, and is an experienced team of experts in infrastructure, frontend and backend development, security and machine learning, as well as a group of in-house trainees. It’s a fairly flat structure allowing the members to have maximum impact within a supportive team.

Our training program is run by Julien, who’s an experienced software developer and mentor, and has produced several highly skilled professionals over the years. The program follows a structured progression framework while adapting to your needs, with a lot of hands-on experience and one-to-one mentoring, ensuring you can learn at your own pace while consistently having an impact on the business.

5 REASONS TO JOIN US:

• Our product is a pioneer in the field, boasting a +55 Net Promoter Score. We build on strong foundations to deliver a solution that is complex on the inside but beautifully simple for the user.
• Unmatched Atmosphere: Experience a culture of camaraderie and trust. We are informal and approachable—even our founder is always available—balancing high expectations with the autonomy to excel.
• Market Exposure: Join a high-growth sector at the forefront of AI recruitment technology. You will partner with global leaders and see the immediate impact of your work on the future of talent acquisition.
• From quarterly socials and monthly briefings, we ensure there is plenty of room for fun and connection outside of the day job.
• We invest in potential. With our rapid growth, many team members have progressed across departments. At Oleeo, we are more powerful together.