From Trainee to Team Lead: Harry’s Career Journey at Cowens

Career progression rarely follows a straight line. At Cowens, it is shaped by opportunity, support, and the willingness to recognise potential early. Few stories illustrate this better than that of Harry, who joined the business with no prior insurance experience and is now leading the Cowens Xpress renewals team.

Starting with Opportunity, Not Experience

Harry joined Cowens in 2022 after spotting a trainee role advertised online. With no background in insurance, the fact that Cowens was actively recruiting and investing in people at the very start of their careers stood out immediately.

That commitment to on-the-job training and long-term development gave Harry the confidence that Cowens was somewhere he could build a career, not just take a job.

Finding the Right Fit and Progressing Quickly

Harry began his career in new business, gaining a strong grounding in the fundamentals of commercial insurance. As his performance developed, managers identified that his strengths were particularly well suited to renewals, where relationship management, technical understanding, and consistency are critical.

That move proved pivotal. Over time, Harry’s knowledge deepened and he naturally became a go-to person within the team – supporting colleagues, sharing insight, and helping resolve challenges. When the opportunity to step into the Renewals Team Lead role arose in September 2024, Harry was ready.

Regular one-to-one meetings, appraisals, and open conversations about career ambitions meant the transition into leadership felt supported rather than daunting.

Leadership Rooted in Culture

For Harry, the culture within Cowens Xpress has been fundamental to both his development and his leadership style. An open, honest environment – where colleagues can approach one another with internal or external challenges – has created a close-knit, high-performing team.

That culture shapes how he leads day to day. He recognises that every individual responds differently to management, and effective leadership means adapting your approach to help each person perform at their best.

The most rewarding part of his journey so far has been seeing that growth reflected in others -supporting team members through problems, building their confidence, and helping them reach their potential.

Working with Family – Professionally

Harry also has the unique experience of working alongside family at Cowens. Rather than complicating things, it has strengthened trust, support, and collaboration. Clear professional boundaries ensure work remains impartial, while the shared experience has brought them closer outside the office as well.

Looking Ahead

Having spent over a year in a leadership role, Harry continues to build his management capability. Cowens has supported this progression through on-the-job training, mentoring from previous team leads, and formal leadership courses.

Looking ahead, Harry’s ambition is clear: to take on greater responsibility, lead larger teams, and continue developing towards a future management role.

Advice for Future Leaders

For anyone considering a role within Cowens Xpress and aspiring to leadership, Harry’s advice is simple: apply yourself. Cowens actively supports career progression, invests in its people, and provides the structure and encouragement needed to turn ambition into reality.