Navigating the Future Together

From Undercover to Insurance: My Journey as a GB Investigator

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By David

October 27 2025


Hi, my name is David, and I've been working as an investigator for over 20 years. My career has taken me on a fascinating journey, from conducting undercover investigations to managing teams and now working once again independently as a GB Investigator. Throughout my experience, I've learned the importance of commitment, growth, and navigating the future together with my colleagues and clients.

The Early Days: Undercover Investigations

When I first started my career, I was eager to gain relevant experience to pursue a position in federal law enforcement. I began as an Undercover Investigator, conducting investigations for various shops in the areas of loss prevention and integrity spotting. It was an exciting time, as I worked to detect employee dishonesty, theft, and procedural and policy violations.

As I gained more experience, I transitioned into the role of a Special Investigator, focusing on insurance fraud cases. This move marked a significant turning point in my career, as I quickly rose through the ranks and found myself supervising a team of 25 employees across New York and New Jersey.

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Every investigator brings a unique perspective and skill set to their assignments, which directly correlates to individual success and recognition. At GB, we’re empowered to work independently, make decisions, and truly own our impact.

Transitioning to Insurance Claims Investigations

After several years in undercover investigations, I made the decision to focus solely on the insurance industry. I spent over 15 years with the same agency, taking on various roles from Special Investigator all the way to Regional Manager. During this time, I honed my skills in investigating insurance claims and developed a deep understanding of the industry.

When the agency I worked for closed its doors during the pandemic, I found a new opportunity with Terrier Claims Services, which was later acquired by Gallagher Bassett. At GB, I continue to investigate claims for potential insurance fraud, managing my own caseload and working independently in the field.

Personal Investigations: A Different Perspective

In addition to my work in insurance claims investigations, I also obtained my own license as a Private Detective, allowing me to focus on personal investigations unrelated to insurance claims. This experience has given me a unique perspective on the differences between personal and insurance-related investigations.

One of the main distinctions lies in the client. In insurance claims investigations, we typically work on behalf of an insurance carrier or a third party representing them. However, in personal, domestic, or family matters, we work directly with individuals or families, helping them navigate difficult and private situations. Both types of investigations can be incredibly rewarding, whether it's fighting against insurance fraud or providing expert assistance to those in need.

The Rewards of Being a GB Investigator

With over two decades of experience in investigations, there are many aspects of my job at GB that I find fulfilling. One of the things I enjoy most is the ability to work independently in the field while managing my own caseload. This autonomy allows me to make decisions about when and how assignments are completed and investigations are conducted. It's an opportunity for each investigator to excel in their work and achieve the best possible outcomes.

Every investigator brings a unique perspective and skill set to their assignments, which directly correlates to individual success and recognition. I take pride in knowing that my work contributes against insurance fraud and helps protect the interests of our clients.

As I reflect on my career journey, I'm grateful for the opportunities I have had to grow and make a difference in the lives of others. My main responsibilities as a GB Investigator include conducting full investigations related to insurance fraud, submitting comprehensive reports, and testifying in court when needed.

But beyond the day-to-day tasks, what truly drives me is the commitment to The Gallagher Way – a set of shared values that guide our work and our interactions with clients and colleagues. It's about growth for the go-getter, always striving to improve and take on new challenges. And it's about a futuristic outlook while working collaboratively to achieve our goals and make a positive impact in the industry.

As I continue my journey as a GB Investigator, I look forward to the opportunities that lie ahead, the people I'll meet, and the challenges I'll overcome. It's a career that has given me so much, and I'm excited to see where it takes me next.