Haydn joined The Gateway Trust as Headteacher at Oakfield Academy in April 2019, bringing with him a wealth of experience of school improvement as a Head and Deputy in his own schools, as well as providing school-to-school support between multi-academy trusts in Lincolnshire, his home county.

Under his direct leadership within the trust, Oakfield Academy underwent a significant turnaround, moving from an 'inadequate' judgement in 2018 to a 'good' OFSTED rating in 2023, with two areas recognised as 'outstanding'. This accomplishment evidences Haydn's dedication and skill in fostering environments where pupils excel academically and become of good character, a particular personal passion.

In 2024, Haydn was awarded fellowship at The Chartered College of Teaching as a formal mark of his achievements, skills and expertise as a teaching professional. Haydn's educational journey is further distinguished by his honours degree in Primary Education, NPQSL and, most recently, the National Professional Qualification for Executive Leadership (NPQEL), obtained in 2023.