Sylvia Mwebesa Kajubi’s journey from firstborn daughter to Deputy Principal of the Insurance Training College is a story of quiet resilience, bold transitions, and the courage to step into roles before feeling ready. Drawing on decades of experience in academia and leadership, she is now using her position to mentor other women, challenging them to seek opportunity, claim space, and rise beyond self-imposed limits.

Sylvia Mwebesa Kajubi has spent more than two decades in academia and leadership, first in the administration of Uganda Christian University and currently at the Insurance Training College, steadily rising through the ranks.

Today, serves as Deputy Principal of the Insurance Training College (ITC) of Uganda, one of the institution’s most senior roles.

She was able to step into roles she did not yet feel ready for, thanks to the support of her supervisors who became mentors. Now, she wants to offer the same kind of help to other women.

Leading without being told

Before titles and offices, or even a mother, a wife, she is a firstborn. A firstborn daughter in a family of five, she always had the younger ones watching to learn something new.

“There is a lot of expectation from firstborns. Even when it is not spoken, it is there,” she says.

It showed up in small, ordinary ways like being the first to go to school, the first to get married, to get it right, or wrong. She comes from an era where everyone took responsibility seriously.

Meals had to be ready, uniforms washed, and younger siblings accounted for. While no one called it or calls it leadership, it was.

“It sharpens you. You learn to organise, to coordinate, to take responsibility,” she says.

A dream borrowed and lost

At school, she was certain she would follow in her father’s footsteps, who was a Chief Accountant in government.

“I admired that. And I loved mathematics, so Accounting made sense. It felt like a plan. But plans, especially young ones, are fragile,” she says.

So when she heard of Bsc. Land Surveying, a new course at Makerere University, she knew she had found her own calling. Four years later, she graduated with a degree in Bsc. in Land Surveying.

“I only practised for about a year. Sometimes, I regret it. But I believe God has a path for everyone,” she says.

Building a life while building a career

Kajubi has worked at the college for close to 11 years now, first as the Academic Registrar and currently as the Deputy Principal.

“Before that, I worked with Uganda Christian University for 15 years. So, in total, I have about 26 years of working experience, right from when I left university. I was fortunate to move straight into employment after campus,” she says.

At UCU, time did not stand still. She moved from Administrative Assistant to Assistant Registrar, and eventually to one of the Academic Registrars, a key academic position at the university.

“I joined UCU as a single person. I got married and had my four children while working there,” she says.

Balancing family and home

Some nights stretched too long. Weekends that disappeared into deadlines. Seasons where she was studying while raising young children.

“There were times we worked until midnight. You can not leave your team when you are their leader,” she says.

Balancing it all needed a lot of grace, but with support of her spouse and family, she did a pretty good job.

“You have to talk to your family. Your spouse, your children, you explain what the journey to the top requires,” she says.

Her children grew up watching her read late into the night while they did their homework.

“They would ask, ‘Mummy, do you also have exams to sit?’ And I would say, yes,” she says, smiling.

At UCU, she found more than a career. She found formation.

“UCU gave me a strong ethical foundation, spiritually and professionally,” she says.

The discomfort of outgrowing a place

Fifteen years is a long time to stay anywhere. Long enough to build, to belong, and to become, but also long enough to outgrow.

“I realised I needed a new challenge. The space was no longer stretching me,” she says.

It is a difficult moment, the one where comfort begins to feel like stagnation. So she did what many hesitate to do. She left. She applied for a few jobs, and one of them being the Insurance Institute of Uganda then, was interviewed, and hired. And then stepped into unfamiliar ground, the insurance sector.

“A completely different industry, but still in education. It was enough to anchor me as I learned everything else from scratch,” she says.

Impostor syndrome

Her rise at the college was steady, from Head of Exams to Academic Registrar then to Deputy Principal, when the position became vacant. She imagined anyone else but her would fill that position when it fell vacant. People around her began to talk.

“Somehow everyone was how suitable I was for the post, I did not think of myself first,” she admits.
Even when the path was clear, she stood just outside it. It took the belief of others to pull her forward.

“Sometimes people see more in you than you see in yourself,” she says.

Breaking ceilings, and naming them

Today, she is the first female Deputy Principal at the college. The first woman to sit on Executive Management since its establishment. Milestones, yes, but for her, they are also mirrors.

“They show you what is missing,” she says.

In Uganda’s insurance sector, women remain underrepresented at top leadership.

“For every five men, you may find one woman,” she says.
And yet, she turns the question inward.

“I think the biggest barrier is ourselves.”

Not lack of ability, not lack of competence, but hesitation.

“We put invisible ceilings on ourselves. We wait and we miss out,” she says.

She recalls a lesson from a leadership programme that gave her a new understanding of personal growth.

“Information, opportunity, and power are never handed to you. You have to seek them, sometimes aaggressively,” she says.

Leading with both firmness and care

In her current role, Kajubi leads with a deliberate philosophy. Participation, inclusion, mentorship and trust. But beneath that is something larger, an understanding of people.

“I listen and we make decisions together. As a woman, you bring empathy. You understand life beyond work,” she says.
She supervises mostly male employees but insists on balance. To empower women in the sector the Women In Insurance (WIN) association provides a platform for mentorship and coaching and ITC also started a women’s leadership program all aimed at grooming more female leaders into top management. A recognition that leadership is not only about output, but also about people.

Background
Kajubi attended Nakasero Primary School, then Merryland High School for six years, and then to Makerere University.