Derek Hobbs, Executive Headteacher (Student Experience)
Derek joined The Two Counties Trust in January 2021 as Headteacher of Wilsthorpe School and began in his role as Executive Headteacher in September 2024.
Alongside continuing to lead the team at Wilsthorpe School, Derek supports other school leaders, with a particular focus on Personal Development and Post-16 Education. Derek also supports the Trust careers team and is passionate about ensuring that every student receives the personalised advice and guidance they need to fulfil their future aspirations.
Derek has previously worked in a range of schools in the East Midlands, including as Headteacher and as an accredited Local Leader of Education (LLE), and also has significant expertise in school inspection.
Derek gained a Joint Honours degree in Music and German at The University of Nottingham. He holds a Master’s degree in Education and the National Professional Qualification for Executive Leadership (NPQEL). He has published a number of teaching resources and was recently the recipient of a scholarship from the Farmington Headteachers Institute, based at Jesus College, Cambridge.
Marie Sly, Curriculum Director
Marie joined The Two Counties Trust in the role of Curriculum Director in September 2020. She supports and coaches school leaders to raise standards of attainment, teaching and learning in the classroom and school effectiveness. Her aim is to ensure that all students achieve their full potential.
Prior to joining the Trust, Marie was an Assistant Principal and Teacher of business and mathematics at Outwood Grange Academies Trust. She enjoyed belonging to a successful leadership team for over 8 years and headed many areas of school leadership including teaching and learning, curriculum development, attainment and progress. Marie is a Administrative Management graduate from the University of Humberside where she studied business, finance, economics and law.
Prior to teaching, Marie worked in the financial services industry for 18 years, mainly in the role of developing and delivering training for professional and technical qualifications in line with strategic national initiatives. Marie brings a diverse range of transferable skills and knowledge to her role, ensuring that students receive the best quality education.
David Plummer, Corporate Services Director
David joined The Two Counties Trust in June 2023 as Corporate Services Director and Chief Finance Officer. He is focussed on delivering an effective and valued shared service to all schools in the Trust.
He is an experienced Chartered Accountant and is the Executive Team Lead for several business functions including Finance, Procurement, Health & Safety, Risk and Estates Management.
David has a broad range of experience as CFO, both within the education sector as well as senior roles within the property, rail and services sectors. He is also a Trustee at Christopher Nieper Education Trust. He is passionate about ensuring that all Two Counties schools have the best conditions to allow students to enhance their future life choices.
David’s legacy sentence is ‘He helped to create a strong Trust.’
Andrew O’Brien, Executive Headteacher (Quality of Education)
Andrew O’Brien joined The Two Counties Trust in September 2022 and in May 2023 was appointed as Executive Headteacher (Quality of Education).
In his current role Andy is working as part of executive team to support Headteachers to ensure that schools are serving their students in the very best way, and guaranteeing the best possible outcomes for all. A focal point of Andrew’s role is to support colleagues in crafting and implement a high-value curriculum. Andrew is also supporting the Trust careers team in providing students with exceptional guidance to support their future ambitions.
Andy has extensive experience, as both Headteacher and Executive headteacher working across Lancashire and Greater Manchester. Working in both inner-city and rural schools has allowed Andrew to work alongside senior leadership teams to deliver excellence in a range of contexts.
After studying Physical Education with Qualified Teacher Status at Gloucester University, Andy taught PE alongside a number of other roles. After leading several PE departments, Andy has undertaken a number of leadership roles in a wide variety of pastoral and curriculum areas. Andy has a particular passion for the development of the curriculum and assessment. Within this area Andy has both supported schools and delivered training with a particular focus around creativity and cultural capital.
Jon Gilbert, Professional Learning and Improvement Director
Jon joined The Two Counties Trust in the role of Professional Development Director in June 2022.
He is responsible for ensuring that the Trust’s strategic anchor of Putting People First is a reality. He works in collaboration with colleagues across the Trust, and outside it, to provide outstanding professional development opportunities for all TTCT staff. Jon ensures that talent within the organisation is developed and can flourish, so that the students in our care receive the best education and experiences possible.
Jon holds a BA(hons) in Philosophy and Theology and a Masters in Theological Research, both from the University of Durham. Prior to joining the Trust, Jon worked for over a decade as an RE, Philosophy, Ethics and Sociology teacher at Dixons Academies Trust. He worked in three separate outstanding schools within the Trust and on the senior teams of two of them, latterly as All-through Vice Principal of Dixons Trinity Chapeltown in Leeds. His main areas of responsibility as a senior leader have been teaching and learning and professional development. Jon has made contributions to a number of national teaching and leadership professional development programmes including the Exemplary Leadership Programme, the Coaching Collective and the Star Institute Instructional Coaching course with Jesse Corburn.
Jon is very proud to be the Trust’s first Professional Development Director as he is driven by the belief that, as professionals, we can all get a little bit better every single day.
Jon’s legacy sentence is ‘He helped me to get better.’
Sarah Bailey, Executive Headteacher (Pastoral)
Sarah Bailey joined The Two Counties Trust in the role of Executive Headteacher (Pastoral) in June 2023.
She works closely with the executive team and leads Headteachers to ensure that schools are serving their students in the very best way, and ensuring the best possible outcomes for all. Not only does she place a high value on academic achievements, but also on ensuring students are developed holistically, affording them access to a wide range of experiences and support outside of the classroom. This ensures they are ready and able to contribute to the world we share as well-rounded citizens.
With her extensive experience, including a successful tenure as Headteacher of an inner-city academy in Nottingham, Sarah brings valuable expertise to the Trust. Her previous senior leadership roles across South Yorkshire, the West, and East Midlands have equipped her with a comprehensive understanding of school leadership. Sarah’s particular areas of passion lie in behaviour, safeguarding, attendance, and inclusion.
After studying Physical Education with Qualified Teacher Status at Sheffield Hallam University, Sarah taught PE and psychology, whilst undertaking a number of leadership roles, largely with a pastoral focus. Her values of humility, kindness and integrity underpin her day-to-day interactions with students and staff alike.
Wesley Davies, Chief Executive Officer
Wesley joined The Two Counties Trust in the role of Chief Executive Officer in January 2021. He works closely with leaders across the Trust to continually improve the outcomes of our students to ensure they have enhanced life choices once they have left our care.
Wesley leads the Executive Team to ensure the Trust has a clear operating model which is both healthy and efficient to deliver the Trust’s vision. He has spent a considerable amount of time developing the culture that exists within our Trust and codifying school improvement so that school leaders are empowered to secure improvement in their schools. Wesley has built a team of domain specialist and has embedded TTCT Empowered to Lead model across the organisation which has overtime become a unique selling point of our Trust.
Working with schools within and beyond The Two Counties Trust is an important part of Wesley’s role. He spends time supporting and learning from other Trusts both locally and nationally.
Prior to joining the Trust, Wesley was an Executive Principal at Dixons Academies Trust where he enjoyed a highly successful career spanning almost 20 years. He was part of three different outstanding academy leadership teams and has led on all areas of school leadership. Wesley has a wealth of experience and credibility having led his own school to an outstanding Ofsted judgement along with supporting various schools to secure improvements. One of his greatest achievements was securing a progress 8 score of +1 for students who were eligible for free school meals.
Wesley is a Theology and Religious Studies graduate from the University of Leeds where he studied a variety of religions with a particular focus on Islam and the philosophy of religion. He has led various Religious Education networks, examined to A level standard, spoken at various conferences and been a guest lecturer on PGCE courses. He occasionally still delivers RE lessons and workshops to students at The Two Counties Trust.
Wesley’s legacy sentence is ‘He inspired me to inspire others’.
Debbie Duggan, Operational Resources Director
Debbie joined The Two Counties Trust in April 2017. Initially responsible for establishing the Human Resources function, she now fulfils the role of Operational Resources Director.
She is the Executive Team lead for a range of business functions including Human Resources, Payroll, Marketing, ICT, Governance and the Trading Company’s Nursery.
Prior to joining the Trust, Debbie held the role of Vice Principal for Organisational Development at Central College Nottingham where she enjoyed a successful career. As part of the senior leadership team she led a range of areas including Human Resources, Quality Assurance, Training and Development & Learning Technologies. As the Ofsted nominee she led the College from Requires Improvement to Good prior to joining the Trust.
Debbie is a Chartered Fellow of the Chartered Institute of Personnel and Development from Nottingham Trent University. She has worked in the education sector for over 20 years in both Secondary and Further Education, specialising in the field of Human Resources in large employers for over 30 years. One of Debbie’s key drivers is to ensure that she delivers high quality, customer focussed business solutions through her teams.
Debbie’s legacy sentence is ‘Her guidance and support were invaluable to others.’
