Executive Assistant to the Head

Employment Type: Full Time

Reports to: The Head

Hours: We anticipate the role being between 0.8 and 1.0 FTE (equivalent to approximately 32-40 hours per week) and are open to discussing working patterns with exceptional candidates.

Working weeks: 52 weeks per year

Closing date: Friday 4 September 2026 at 9:00am

About the role:

Oakham School is seeking to appoint an exceptional Executive Assistant to provide high-quality, proactive and confidential support to the Head.

This is an exciting opportunity for someone who is highly organised, digitally confident, emotionally intelligent and keen to play a central role in the smooth running of the Head’s Office. The successful candidate will be a trusted and professional support to the Head, helping to manage her diary, communications, meetings, priorities and follow-up actions.

This is not simply a traditional administrative role. We are looking for someone who can think ahead, use initiative and anticipate what needs to be done. The successful candidate will be able to manage competing demands calmly, prepare clear and accurate briefing materials, handle sensitive information with discretion and build effective relationships with colleagues, parents, governors and external partners.

The role could suit an experienced Executive Assistant, Personal Assistant or senior administrator looking for a varied and high-profile role. Equally, we welcome applications from exceptional graduates or early-career professionals who can demonstrate strong organisational skills, excellent judgement, emotional intelligence and a genuine desire to learn while working closely alongside the Head of a leading independent school.

The ideal candidate will be proactive, polished, discreet and solutions-focused, with excellent attention to detail and the confidence to make things happen. They will be comfortable working at pace, able to prioritise effectively and committed to supporting the Head in a way that is professional, calm and forward-thinking.

We are open to considering applications from candidates seeking either a full-time role or a reduced working pattern of approximately 0.8 FTE. Some flexibility may also be available during School holiday periods, subject to the operational needs of the Head's Office.

Benefits Package:

Pension scheme, healthcare cash plan, free meals during term time and use of pool and gym, on-site parking, cycle to work scheme, Support staff fee remission.

How to Apply

Full details of the role can be found on the attached Job Description and Person Specification. To apply, please visit the Oakham School website and complete the Application form attaching a CV and covering letter.

We reserve the right to interview on an ongoing basis and interviews may take place before the closing date, therefore early applications are advised.

Safer Recruitment:

Oakham is committed to safeguarding and promoting the welfare of children and young people and expects all staff to share this commitment. Under current legislation, we are required to advise applicants that this appointment will be subject to a satisfactory Enhanced Disclosure with the Disclosure & Barring Service. Details of any criminal record (spent or unspent, due to exemption from the Rehabilitation of Offenders Act 1974) must be disclosed at interview. Only relevant convictions and other information will be taken into account so disclosure need not necessarily be a bar to obtaining a position at Oakham School.

Job Types: Full-time, Part-time, Permanent

Pay: £30,000.00-£35,000.00 per year

Benefits:

• Company pension
• Discounted or free food
• On-site parking

Work Location: In person