Celebrations are in order after Courtney Simm hit the decade milestone marker at Winn Group recently.

Starting back in 2015 in the Customer Service Team, her career path at Winns has taken her to the MOJ Portal team before switching to Vehicle Damage where she currently resides as a Senior Supervisor.

A valued member of the Pre-Lit department, Courtney’s contributions haven’t gone unnoticed.

Chris Cullingworth, Winn Group Associate Director and Head of VD - Pre-Litigation, said: “It has been a pleasure working with Courtney over the years. She is hard working, determined and very knowledgeable of all things credit hire.

“This has allowed Courtney to go from strength to strength with multiple promotions within the Vehicle Damage teams.”

We caught up with Courtney to reflect on her career journey at Winns to date:

What do you remember about your interview / initial steps here at Winns?

I remember starting in the Customer Service Team under Lucy Donnelly, handling queries for all departments. I was always eager to learn as much as I could, constantly asking the handlers questions so I could understand the reasoning behind everything and confidently assist clients myself.

Looking back, I probably drove them a bit mad with how curious I was!

One day, while chatting at the coffee machine, our former Complaints Officer suggested I apply for the MOJ Paralegal role in Amy Graham’s department - she said she thought I’d be great at it.

At the time, I was still in my probation period and honestly never thought I’d get the position. So, when I was offered the role, I was absolutely thrilled! I joined Catherine Walker’s team, and that’s really where my journey with Winns began.

What were your career expectations when you first started?

Honestly, my main goal when I first joined was to get into litigation. It was something I’d had my sights set on well before I came to Winns, and I feel really fortunate that it’s been such a major part of my time here.

I’ve gained a huge amount of practical experience and learned so much from some truly outstanding people. I never expected to get involved in litigation so early, but I was absolutely thrilled when the opportunity came along - it’s shaped my career in ways I couldn’t have imagined.

As for reaching 10 years at the company, once I started learning and realised just how many different areas I could develop new skills in, it definitely felt possible. I’ve had the chance to work in PI, credit hire, both Part 8 and Part 7 litigation, staff management, and even Scottish cases.

Every role has been a learning curve and has added something new to my skillset, and I love that there’s always something fresh to explore and grow in here.

What element of Winn Group life has encouraged you to continue here?

What really encourages me to stay at Winns is that no two years are ever the same. The company is always evolving and growing, which keeps things interesting and engaging. I’m someone who doesn’t like standing still - I’m constantly looking to improve, learn new skills, and take on fresh challenges.

Doing the same repetitive tasks every day can get mundane, but thankfully, that’s never the case here. We’re always pushing forward, adapting, and growing, which really matches what I want from my career.

And, of course, the people make a huge difference. Over the years, I’ve been lucky to meet some incredible colleagues who have made this experience rewarding, both professionally and personally.

Do you feel supported in your career?

Absolutely. I’ve been very fortunate to have spent most of my time at Winns under the management of Chris Cullingworth, who has been a great source of support and instrumental in advancing my career.

Performance reviews and constructive feedback have played a key role in helping me set clear goals and monitor my progress, showing me that my development truly matters, while also helping me overcome self-doubt (which was often).

The company’s commitment to professional development is evident through its training sessions and mentoring programs, all of which have significantly contributed to expanding my skills and growing in my role, something I truly appreciate.

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