Exploring Insurance Careers: Meet Robert Caldwell, Regional Claims Supervisor


In the thick of a job-hunt, finding a career that you’re passionate about can feel nearly impossible. However, the perfect role could be within your reach – if you know where to look.

As a new graduate, Robert Caldwell knew that he wanted to help people with his career, but he never thought that he’d find that opportunity in the insurance industry. Nevertheless, after testing the waters in a number of industries, he found an amazing career in insurance claims.

Today, Robert works as a Regional Claims Supervisor. He absolutely loves what he does, and he shares some of his insights into this egg-citing field.

Finding a place in insurance

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Robert Caldwell
Regional Claims Supervisor
Career Connections

During his time in university, Robert says he mainly focused on his studies, and only started to consider his career aspirations in his third year. After graduation, he made the leap from his small town home of Sudbury, ON and moved to the big city of Toronto.

“All I knew was I wanted to make a difference and help others,” says Robert. “I never really considered insurance at all up until some fortuitous twists of fate put me in a position with ties to the industry.”

Robert’s first job was with a major car company, which gave him his first look at the Insurance field. During his time there, he got to know the some of the insurance adjusters. These relationships gave him his first glimpse into the field.

“I would always ask questions about what their day was like and what type of opportunities were in their field,” says Robert. “They always said they enjoyed their job and that piqued my interest in the insurance industry.”

His colleagues’ endorsements, coupled with his desire for a stable career, led him to his first role in claims administration. Robert loved interacting and supporting clients on a daily basis – in fact, despite the many diverse career opportunities in insurance, he still works in the claims field to this day.

“Over my decade in the industry, I have come to realize insurance professionals are about helping people,” says Robert. “We provide security to our clients and help them get back to the lives they knew before calling their insurance company to file a claim.”

A typical day

Presently, Robert holds the role of Regional Claims Supervisor at his organization. He and his team of claims adjusters are responsible for helping clients who have experienced an incident get back to the financial state they were in and get their lives back on track, whether it be through repairing property or paying for medical treatment. Claims adjusters are also involved in defending customers against legal actions that may arise in their case.

“The most challenging part of my job is balancing my to-do list every day,” says Robert. “A claims department is a high paced and sometimes hectic place. However, it is the challenge that also keeps every day interesting.”

Insurance employers regularly welcome new professionals from a range of different backgrounds, providing in-depth training to ensure they have the tools they need to succeed. During his early career in claims, Robert’s employer provided extensive support in the forms of in-class, theoretical, and practical training with a focus on customer service, analytical thinking, and financial management.

However, Robert’s learning experience didn’t end there. After being in the Insurance field for 10 years, he still has opportunities to expand his knowledge in the field. Recently, he completed his Chartered Insurance Professional (CIP) designation. On top of that, he is presently enrolled in the Fellowship program at the Insurance Institute of Canada.

“It was very apparent to me during my early years in the industry that my colleagues took their careers very seriously and wanted to impart knowledge to the younger generation more than anything,” says Robert. “They were a wealth of knowledge that guided my technical training in my first positions.”

Career advice for new grads

Like Robert, many new graduates wind up in the world of Insurance by chance. Only then do they discover the amazing opportunities this industry has to offer – stability, mentorship, and lifelong learning to name a few. However, Robert says that he hopes more young professionals will aspire to enter this field, and start their career preparations early.

“Time and time again, we hear people just ‘fall into’ insurance as opposed to it being a career aspiration,” says Robert. “The industry needs dedicated and conscientious people in order to continue on our quest of delivering peace of mind and security to our clients.”

Fortunately, Insurance is extremely versatile. Whether you consider yourself a wordsmith, numerically-savvy, or an expert relationship-builder, this field is sure to have a role that suits you. Robert says that taking on jobs in customer service is a great start for any student, as this field is focused on providing services and support for customers and clients.

Whether you work with them directly or not, delivering services to people in such a critical time of need can be a bit intimidating at first. Luckily, the Insurance field is staffed with knowledgeable professionals – many of whom have been in the industry for the majority of their careers!

Robert recalls a critical piece of advice he’d received from a manager early in his career, that has guided his career: “‘Don’t be afraid to make a decision, as along as the decision you are making is well thought out and you are not afraid to have your name attached to it.’”

Confidence is key in this field. However, that doesn’t mean your learning stops there. Employers in this field are committed to building up knowledgeable and committed professionals, and more often than not, they are open to covering expenses if you are looking to earn an additional designation.

“The industry changes constantly, and as professionals we need to keep abreast of the changes so that we can deliver exceptional service,” says Robert.

For Robert, he intends on continuing his career in the Insurance industry. He loves developing and mentoring great Insurance adjusters, and he encourages students and grads to consider starting a career in this field. Not only is it exciting and brimming with opportunities, it’s a rewarding path to pursue as well.

“More than anything, I love getting a heartfelt and genuine “thank you” when going above and beyond for my clients,” says Robert. ”With any luck, not only will I stay in the insurance industry, but also remain in the claims discipline for my entire career.”

Ready to eggs-plore an insurance career? Check out Career Connections’ Employer Page for more information!