My professional journey began in insurance claims. After serving in the military, I spent three years at The Hartford, where I worked my way up to an insurance claims adjuster. While I enjoyed the work, the pay at the time wasn’t enough to support my long-term goals. So, I made the decision to go back to college and pursue a new path in IT.

Fast forward to 2005, after the dot-com bust, I returned to the insurance industry and joined Kemper Insurance. Over the next five years, I handled a wide variety of claims, from minor fender benders to complex liability with minor injuries. One of the most defining moments of my career came when a colleague suffered a heart attack, leaving a critical gap in our team. Without hesitation, I stepped into a fast-paced Total Loss Desk position, managing high volumes of claims for over four months. There was no training, no onboarding – just the immediate need for someone to step up. I adapted quickly and nearly matched the pace of my colleague, a 17-year veteran.

This experience reinforced a lesson I learned in the military: when challenges arise, you don’t run from them – you run toward them. Whether it’s investigating a claim, negotiating settlements, or stepping into a new role at a moment’s notice, I’ve always been the one to take on the challenge. Is that a character flaw or an asset? I’ll let you decide.

During my time in insurance claims, I learned how to help people navigate the tricky process of estimating their vehicle’s total loss.

Here’s a guide I wrote to help you - How to Handle a Total Loss Vehicle.

After leaving The Hartford, I went back to college and earned an Associate of Applied Science degree in IT. While in school, I worked hard to gain hands-on experience, building up two years of IT work experience by the time I graduated. That effort paid off when I landed my first major IT role as a Workstation Engineer for a Microsoft Solution Provider. There, I honed my skills in troubleshooting, system optimization, and client support.

After two years, I moved on to a Network Administration role at (CIBC) a nationwide bank, where I managed complex systems and ensured network stability across multiple locations. My time in IT taught me how to think critically, solve problems efficiently, and communicate effectively with people who often felt overwhelmed by technology. These skills have been invaluable throughout my career, no matter the industry.

Between my time in IT and insurance claims, I’ve developed a unique combination of skills: the ability to troubleshoot and the ability to investigate. From IT, I learned how to break down complex problems and find solutions. From claims handling, I learned how to dig deep, ask the right questions, and uncover the truth.

Together, these skills have turned me into a bit of a “gum shoe” investigator, tip-toeing on the level of Columbo-style fact-finding. What’s next? Learning how to profile a psychopath? Who knows – but I’m always up for the challenge.