This is the first in our series introducing the leadership that will shape St John's College as we move into 2026 and beyond. These are the individuals who will steward our values, support our community, and uphold what it means to be a Johannian.
As we look ahead to 2026, when Dale Jackson will join us as the 17th Executive Head, let us introduce you more personally to the man who will lead our school into its next chapter — a man who chose St John's not once, but twice.
Dale's first choice came two years ago, not as a headmaster, but as a parent. Long before his appointment was even on the horizon, he and his wife, Sarah, faced the same decision many of you have made: where to send their son to school. Their eldest son, Matthew, is now thriving in the College, and that decision tells you everything you need to know about Dale's belief in what we do here.
"St John's stands apart as a very special school," Dale says, reflecting on that choice. "It is a school with a soul, a school where our young men and women are taught to think with a global mind and an African heart."
"St John's stands apart as a very special school. It is a school with a soul, a school where our young men and women are taught to think with a global mind and an African heart."
Dale's journey to education leadership is unusual. A Chartered Accountant who trained at PricewaterhouseCoopers, he spent years in sports management, even working with the Springbok rugby team, and then in healthcare. He built businesses, lived abroad, and enjoyed considerable success. But something was missing. He felt what he describes as a calling to "return to South Africa and make a difference."
That calling led him back to his old school, Jeppe High School for Boys, where he began volunteering in 2009. What started as giving back evolved into something far deeper, a complete career change. He returned to university to earn his PGCE teaching qualification and has spent the past 17 years transforming not just an institution, but thousands of young lives.
Those who know Dale describe a leader of deep integrity and authenticity. During their adoption of youngest daughter Kate, a psychologist noted that Dale has "grandiose ideas, bordering on the delusional" about changing the world. Rather than being offended, Dale embraced it. "I truly do wish to change the world, live a life of meaning and make a difference in all that I do," he says. It's this idealism, combined with practical experience, that defines his leadership.
Dale is a devoted family man. He and Sarah, an obstetrician and gynaecologist, have four children: Mackenzie (15), Matthew (13), Rhys (11), and Kate (8). They understand firsthand the partnership between school and home that makes education work. "If you want to outsource the education of your son to a school, we are not the place for you," he told prospective families at our recent Open Day. "But if you wish to partner with us in the glorious adventure of your son's development, then St John's is home."
His educational philosophy aligns closely with our values. He believes passionately in holistic education, that "the lessons learned outside the classroom are just as important as those within it, where manners matter as much as marks." He speaks eloquently about creating "balanced human beings" and preparing our students for the road ahead, not preparing the road for them.
Choose a school for your child where they are happy, where they are placed at the centre of all decisions, and where they can become the best version of themselves, whatever that may be.
Dale champions what he calls "traditional" education, though not in the sense the word has acquired in recent years. For him, traditional means values-based, character-focused, and unashamedly committed to excellence. "Choose a school for your child where they are happy, where they are placed at the centre of all decisions, and where they can become the best version of themselves, whatever that may be."
What drew him to accept this role is telling. Beyond the alignment of educational philosophy and values, it was something deeper: "St John's is a school with a soul." As someone who already experiences this daily as a parent, he understands what makes our community special.
As someone who grew up in the Methodist faith and as a founding trustee of the Theo Jackson Scholarship Fund, now the largest single-school scholarship for boys in South Africa, Dale lives his values of service, inclusion, and transformation.
We are genuinely honoured that Dale has entrusted us with his son's education, and equally honoured that he has chosen to lead our school into its next chapter. His appointment represents not just continuity of values, but a deeply personal commitment to a community he already loves.
Please join us in welcoming Dale and the entire Jackson family as they prepare to make St John's College not just their son's school, but their professional and spiritual home.