Director of Development and Engagement
Full time
Starting ASAP
Welcome from the Headmistress
Dear Candidate
Thank you for your interest in the position of Director of Development and Engagement at Headington Rye Oxford.
This is an exciting moment in the life of our school. Following the coming together of Headington School and Rye St Antony, we are building a distinctive educational community that combines academic excellence, creativity, ambition and care. We are proud of our history, inspired by our future, and committed to ensuring that a transformational education remains accessible to talented young people regardless of financial circumstances.
At Headington Rye Oxford, we believe education changes lives. Our pupils are intellectually curious, confident, compassionate and ready to make a positive difference in the world. We seek to nurture not only academic success but also character, resilience, creativity and leadership.
As we look to the future, philanthropy and engagement will play an increasingly important role in helping us realise our ambitions. We are committed to expanding our bursary provision, strengthening our alumni and parent networks, in parallel with building a culture of lifelong engagement that connects generations of the Headington Rye community.
The Director of Development and Engagement will join us at a pivotal stage in our journey. Working closely with the new Head, the Senior Leadership Team, Governors and our wider community, they will help shape a compelling vision for philanthropy and engagement that enables the school to thrive for generations to come.
This is an exceptional opportunity for an ambitious and strategic leader who combines fundraising expertise with relationship-building excellence.
I look forward to meeting you during the recruitment process.
Yours sincerely,
Caroline Jordan Head
Executive Summary
We are seeking an outstanding relationship-builder and strategic leader who combines fundraising expertise with emotional intelligence, ambition and authenticity.
The successful candidate will be an outstanding communicator who is able to inspire confidence across a wide range of audiences. Importantly, they must understand how to build meaningful relationships that lead to long-term engagement and philanthropic support.
Reporting directly to the Head and serving as a member of the Senior Management Group, the Director of Development and Engagement will provide strategic leadership for all aspects of fundraising, alumni relations and stakeholder engagement.
The successful candidate will develop and implement a comprehensive development strategy that supports the school's long-term ambitions and builds a culture of philanthropy across the entire community.
This role combines strategic leadership with hands-on relationship management and external representation.
The Director will work closely with:
- The Head
- Governors
- Senior Leadership Team
- Commercial Director
- Alumni and supporter networks
- Current and former parents
- Major donors and prospective benefactors
- Corporate and charitable partners
Development and Engagement at Headington Rye Oxford
The Development and Engagement Office plays a central role in strengthening relationships across the School's community and supporting its long-term strategic ambitions.
Working across philanthropy, alumni relations, parent engagement, partnerships and communications, the team builds meaningful connections with former pupils, current and former parents, friends of the School and philanthropic supporters.
The School is entering an exciting phase of development. As a newly unified community, there is significant opportunity to establish a shared culture of engagement and philanthropy that reflects the aspirations of Headington Rye Oxford.
Key strategic priorities include:
- expanding transformational bursary provision
- growing philanthropic income
- developing a major gifts programme
- increasing regular and legacy giving
- strengthening alumni engagement
- building meaningful parent and community partnerships to support pupils’ transition to the world of work
- creating lifelong relationships with supporters
The Director of Development and Engagement will lead this work and help establish a sustainable platform for future growth.
Role Description
The Director of Development and Engagement is a full-time, permanent, all-year round position.
Key responsibilities
Fundraising and philanthropy
- develop and implement the School's fundraising strategy
- lead major gift fundraising activity and personally manage a portfolio of high-value prospects
- build and maintain relationships with alumni, parents, foundations and philanthropic supporters
- create compelling cases for support aligned with strategic priorities
- grow income through major gifts, regular giving, trusts and foundations, and legacy giving
- develop stewardship programmes that demonstrate the impact of donor support
- identify and cultivate new philanthropic opportunities
Strategic leadership
- develop a long-term engagement and philanthropy strategy
- advise the Head and Governors on fundraising opportunities and sector trends
- monitor performance against agreed objectives and income targets
- ensure fundraising activity supports the school's strategic plan
- produce reports for Governors and relevant committees
Alumni and community engagement
- lead alumni relations and lifelong engagement programmes
- strengthen connections across both Headington and Rye alumni communities
- develop regional and international alumni networks
- deliver an engaging programme of events, reunions and networking opportunities
- create volunteering and mentoring opportunities for alumni
Parent and stakeholder engagement
- develop meaningful engagement opportunities for current and former parents
- strengthen relationships with supporters and advocates
- work collaboratively across the School to promote engagement initiatives
- ensure engagement activity is integrated into the life of the School
Budget and performance management
- lead and develop the Development and Engagement team
- foster a culture of ambition, professionalism and collaboration
- manage departmental budgets and resources effectively
- ensure compliance with GDPR, fundraising regulations and best practice
- maintain accurate prospect and donor management systems
Person Specification
Qualifications and Experience
Essential
- significant experience in fundraising, development or advancement
- proven track record of securing major gifts
- experience of developing and implementing fundraising strategies
- experience of leading teams and managing budgets
Desirable
- experience within education, higher education, arts or charity sectors
- campaign fundraising experience
- alumni relations and engagement expertise
- knowledge of independent schools
Personal attributes/skills
- strong stakeholder management and relationship-building skills
- excellent written and verbal communication skills
- strategic and visionary thinker
- exceptional interpersonal skills
- influential and persuasive communicator
- collaborative leadership style
- high levels of integrity and professionalism
- resilience, energy and enthusiasm
- commitment to the values and mission of Headington Rye Oxford
Terms of Appointment
Type of Contract
Permanent, full time, all year round.
Benefits
Pension
Contributory membership of the School’s Support Staff Pension Scheme with a School contribution of up to 9.95 per cent upon successful completion of six months’ service.
Fee remission
In accordance with the School’s policy, which may be subject to change, up to 50 per cent fee remission for pupils attending Headington Rye Oxford and up to 20 per cent fee remission for boys attending Magdalen College School (under a reciprocal agreement) and subject to the terms of their policy. Fee remission is calculated on the number of weeks and hours worked and is pro rata for part-time staff who work at least 50 per cent of a normal working week.
Salary
£65,000 per annum
30 days annual leave plus eight bank holidays.
Additional Benefits
Free school lunches are provided. All staff have access to a broad programme of wellbeing activities. The programme currently includes access to the School’s gym and swimming pool, weekly Step and Tone and Zumba classes and regular staff social activities such as Book Club and Staff Choir. Staff also benefit from free access to the Employee Assistance Programme, a free, confidential helpline that offers advice on a range of issues. Free restricted parking is available for all staff on site.
Appointment Process and How To Apply
Applicants should submit an application form and a covering letter detailing their skills and experience to recruitment@headingtonschool.com
- Applications will only be accepted from candidates completing the application form in full. CVs will not be accepted in substitution for completed application forms. However, they may be sent in addition to the application form.
- We will seek references on shortlisted candidates and will approach previous employers for information to verify particular experience or qualifications, before the interview. References will ask about your suitability to work with children.
- If you are invited to interview you will receive notification outlining the interview process and guidance regarding the documentation you are required to provide.
Application deadline: Friday 24th July 2026
Interviews: to be arranged shortly after closing date
Applications are reviewed and shortlisted on a rolling basis and we reserve the right to interview, appoint and close adverts early depending on the volume of applications we receive. We therefore encourage you to apply at the earliest opportunity to avoid disappointment as once we have closed a vacancy you will be unable to submit your application form.
All appointments are subject to satisfactory completion of all employment checks, ie references, Disclosure and Barring Service, medical questionnaire, Right to Work in the UK. Headington Rye Oxford is an equal opportunities employer and is committed to safeguarding and promoting the welfare of children and young people. Applicants must undergo child protection screening, including checks with past employers and DBS and barred lists checks. The School expects all staff and volunteers to share this commitment.
