Oleeo
Trainee System Administrator 2026
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Trainee System Administrator 2026
What You’ll Be Doing
Oleeo is seeking an entry-level Trainee System Administrator who is:
- An IT Support professional,
- An apprentice, or
- An 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.
This is a very hands-on role, where you will:
- Provide immediate operational relief to our infrastructure team,
- Make a real impact early on,
- See your responsibilities grow systematically through our training programme.
Key responsibilities include:
- Ensuring our internal environments and platforms run smoothly to support:
- Next-generation online Software-as-a-Service (SaaS) products in recruitment.
Using our action-oriented training methodology, your progression will focus on:
- Executing real-world technical workflows,
- Achieving measurable professional development goals.
From the first day of your training, you will:
- Be part of a wider technical operations team,
- Work closely with:
- System administrators,
- Developers,
- Product management,
- Grow in strategic responsibilities alongside your technical skills.
This is a hybrid role, with the expectation to:
- Be in our office in Wimbledon, South London once a week for IT Support tasks.
Key Skills & Experience
Must have:
- Some demonstrable experience in IT Support, whether gained in:
- Formal employment,
- Apprenticeships,
- Personal time.
- A proven track record or strong background in:
- Hands-on IT troubleshooting.
- Curiosity and analytical problem-solving skills.
- Eagerness to learn.
- Demonstrable critical thinking.
- Outstanding attention to detail.
- Evidence of problem-solving and the ability to:
- "Grok" things.
- Ability to:
- Work in the UK without any restrictions.
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Security Clearance Required in this role, meaning:
- 5-year UK residency history is required.
Who Are Oleeo?
Oleeo means "a diverse collection of things that together, make something beautiful." This is how we see ourselves:
- A diverse team of technology, and talent acquisition professionals, coming together to achieve something beautiful.
We are proud to be a team of individuals who collectively deliver:
- Powerful data-driven automation,
- For fast, efficient, engaging, and inclusive recruitment.
Our purpose and passion is to:
- Support organisations in engaging and hiring great diverse talent,
- Do so quickly, efficiently, and without bias.
As pioneers in recruitment software, our solutions are designed to:
- Accelerate and improve the entire recruiting process,
- Create a more:
- Meaningful,
- Engaging,
- Transparent experience for candidates,
- Enable recruiters to become the very best they can be.
We are:
- Established for over 20 years,
- Offices in:
- London,
- New York,
- A presence in Asia.
- Offices in:
Some of our world-renowned customers include:
- The NHS,
- Morgan Stanley,
- The Metropolitan Police,
- Amazon,
- Bank of America.
What’s It Like to Work Here?
We foster a terrific, diverse, flexible culture, where people are empowered to:
- Work in ways that suit them best,
- Love being part of Oleeo, thanks to our authentic environment.
Our values are centred around:
- People—ourselves and our customers.
The technical team consists of:
- About 30 people,
- Experts in:
- Infrastructure,
- Frontend and backend development,
- Security,
- Machine learning,
- A group of in-house trainees.
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The structure is fairly flat, allowing members to:
- Have maximum impact within a supportive team.
Our training programme is led by:
- Julien, an experienced:
- Software developer,
- Mentor,
- Produced several highly skilled professionals over the years. The programme follows:
- A structured progression framework,
- Adapting to your needs,
- Includes:
- Much hands-on experience,
- One-to-one mentoring,
- Ensures you can learn at your own pace, while:
- Consistently having an impact on the business.
Check out Julien’s profile → linkedin.com/in/julienfiegehenn.
5 Reasons to Join Us
-
Innovative Product
- Our product is a pioneer in the field, boasting a +55 Net Promoter Score.
- We build strong foundations for a solution that is:
- Complex on the inside,
- Beautifully simple for the user.
-
Unmatched Atmosphere
- Experience a culture of:
- Camaraderie,
- Trust.
- Be informal and approachable—even our founder is always available.
- Balance: High expectations with the autonomy to excel.
- Experience a culture of:
-
Market Exposure
- Join a high-growth sector at the forefront of AI recruitment technology.
- Partner with global leaders and see:
- Immediate impact of your work on the future of talent acquisition.
-
A Vibrant Community
- Quarterly socials and monthly briefings ensure plenty of room for:
- Fun,
- Connection outside of the day job.
- Quarterly socials and monthly briefings ensure plenty of room for:
-
Opportunities
- We invest in potential:
- Many team members have progressed across departments.
- At Oleeo, we are more powerful together.
- We invest in potential:
“It took my CV and asked me questions relevant to understanding what kind of jobs to suggest for me. Suggestions were almost perfect. Jobs were exactly what I’ve been looking for.”
Jessica, London
Skills