Executive Assistant to the Head

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. Oakham School is committed to safeguarding and promoting