Find a job 
Featured Companies 
Featured Universities 
For Companies At a Glance
- Tasks: Lead a vibrant prep school, inspiring excellence in teaching and nurturing student growth.
- Company: Alleyn’s Oakfield, part of a prestigious group with over 400 years of educational excellence.
- Benefits: Beautiful surroundings, excellent transport links, and a supportive community.
- Why this job: Shape the future of a flourishing school and make a real impact on young lives.
- Qualifications: Dynamic leadership skills and a passion for education and child development.
- Other info: Join a collaborative environment with opportunities for strategic growth and development.
The predicted salary is between 36000 - 60000 ÂŁ per year.
The Alleyn’s Schools Group is delighted to invite applications for the next Head of Alleyn’s Oakfield, a joyful, warm and ambitious prep school for children aged 4–11 in the heart of leafy West Dulwich. In August 2025, Oakfield Prep formally became Alleyn’s Oakfield, joining a family of schools with more than 400 years of educational excellence, a distinctive values‑led culture, and a shared commitment to inspiring every pupil and member of staff to be “all they can be.”
This is a pivotal and exciting moment for the school. With recent and future investment in buildings and facilities, a vibrant curriculum, a thriving co‑curricular programme and a nurturing, community‑centred ethos, Alleyn’s Oakfield is exceptionally well‑placed for continued growth and strategic development within the wider Alleyn’s group.
We are seeking a dynamic, inspiring leader who brings clarity of vision, authenticity and energy. The next Head will lead the strategic development and day-to-day operations of the school, and champion excellence in teaching, learning and pastoral care, modelling Alleyn’s ROCCK values and fostering a culture in which children feel known, supported, stretched and celebrated.
They will provide clear, ambitious leadership aligned with the overarching aims of the Alleyn’s School Group, working closely with senior colleagues to enhance alignment, maintain high standards and ensure that Alleyn’s Oakfield thrives within a rapidly evolving educational landscape. They will be a visible, trusted and emotionally intelligent presence, able to communicate with warmth while cultivating a collaborative, joyful environment for staff and pupils alike.
This is a rare opportunity to lead a flourishing, ambitious school full of potential. With beautiful surroundings, excellent transport links into central London and the strength and shared purpose of the wider Alleyn’s group, Alleyn’s Oakfield offers an exceptional platform for an inspiring leader to shape a school that is both deeply rooted and confidently future‑facing.
To apply, please submit a completed application form, CV and a covering letter by 9.00am GMT Monday 2 March online via the button below, where you can also download the candidate brief.
Alleyn’s Oakfield is committed to safeguarding and promoting the welfare of children, and applicants must be willing to undergo child protection screening appropriate to the post, including checks with past employers and the Disclosure and Barring Service (DBS).
Head (Oakfield School) employer: ALLEYNS SCHOOL DULWICH
Contact Detail:
ALLEYNS SCHOOL DULWICH Recruiting Team
StudySmarter Expert Advice 🤫
We think this is how you could land Head (Oakfield School)
✨Tip Number 1
Network like a pro! Reach out to current or former staff at Alleyn’s Oakfield and ask about their experiences. This insider info can give you a real edge in understanding the school's culture and values.
✨Tip Number 2
Prepare for the interview by aligning your vision with the school's mission. Think about how you can embody the ROCCK values and be ready to share specific examples of how you've done this in your previous roles.
✨Tip Number 3
Show your passion for education! During your discussions, let your enthusiasm for nurturing young minds shine through. Schools want leaders who are genuinely excited about making a difference in children's lives.
✨Tip Number 4
Don’t forget to apply through our website! It’s the best way to ensure your application gets noticed. Plus, it shows you’re serious about joining the Alleyn’s family.
We think you need these skills to ace Head (Oakfield School)
Some tips for your application 🫡
Get to Know Us: Before you start writing, take a moment to really understand what Alleyn’s Oakfield is all about. Dive into our values and culture, and think about how your vision aligns with ours. This will help you craft an application that truly resonates with us.
Tailor Your CV: Your CV should be a reflection of your unique journey and achievements. Make sure to highlight experiences that showcase your leadership skills and commitment to education. We want to see how you've made a difference in previous roles!
Craft a Compelling Cover Letter: Your cover letter is your chance to shine! Use it to tell us why you're the perfect fit for the Head of Alleyn’s Oakfield role. Share your passion for education and how you plan to inspire both staff and pupils. Keep it warm and engaging!
Apply Online: When you're ready, make sure to submit your application through our website. It’s the easiest way for us to receive your materials and ensures everything is in one place. Don’t forget to double-check your submission before hitting send!
How to prepare for a job interview at ALLEYNS SCHOOL DULWICH
✨Know the School's Values
Before your interview, take some time to really understand Alleyn’s ROCCK values. Think about how these values align with your own leadership style and experiences. Be ready to share specific examples of how you've embodied similar values in your previous roles.
✨Showcase Your Vision
As a candidate for Head of Oakfield, it's crucial to articulate your vision for the school. Prepare to discuss your ideas on strategic development and how you plan to enhance teaching and pastoral care. Make sure your vision reflects the nurturing and ambitious ethos of the school.
✨Engage with the Community
Demonstrate your understanding of the importance of community in a prep school setting. Be prepared to talk about how you would foster relationships with staff, pupils, and parents. Share any past experiences where you successfully built a collaborative environment.
✨Be Emotionally Intelligent
In your interview, showcase your emotional intelligence by being warm and approachable. Use active listening skills and respond thoughtfully to questions. This will help convey that you can create a supportive atmosphere for both staff and students, which is key for this role.
