The Gallagher Way

My Journey as a New Supervisor at Gallagher Bassett

brian calogero testimonial tile 1

By Brian

March 26 2026

When I joined Gallagher Bassett, I walked in as a new supervisor, paired with a new team, learning a new client, and adjusting to a new way of connecting in a remote world.

My team pretty much consists of all new hires, so we were all learning the systems and everything together. There’s something powerful about growing from the ground up. We were learning how to trust each other, lean on each other, and build a culture of collaboration from scratch.

And as a new leader, that shaped the way I wanted to show up for my team. Being able to teach them as I'm learning has been really productive. Leadership, I quickly realized, wasn’t about having every answer. It was about being present, honest, and committed to finding the answers together.

Navigating the Unknown

Taking on a supervisory role while simultaneously onboarding a brand‑new client can feel overwhelming. There were moments early on when the uncertainty weighed heavily. But those concerns didn’t last long. What I found instead was a community ready to lift me up.

There has always been a helping hand for me when I either didn't know an answer or if I just wanted to reach out to confirm something. That willingness to step in, support, and guide is one of the biggest reasons I feel grounded here.

I joined during a significant moment of change for the company. Systems were being upgraded. Processes were being re-engineered. The culture was moving with purpose toward the future.

1

Starting during this period gave me clarity about the kind of supervisor I want to be. I want to be a resource and make their job easier. I try and be an asset to them. I try and take away roadblocks.

In moments that matter, you matter

Joining Gallagher Bassett wasn’t just a career move. It was an opportunity to rediscover what leadership can be. It’s about accessibility, humility, and the willingness to grow with your people.

And that’s exactly what I’ve found: a team willing to learn together - a culture built on availability, support, and a company embracing innovation and change.

Most importantly, Gallagher Bassett is a place where being a new leader isn’t a limitation. It’s an opportunity to shape something better.

Explore Careers At Gallagher Bassett

Gallagher believes that all persons are entitled to equal employment opportunity and prohibits any form of discrimination by its managers, employees, vendors or customers based on race, color, religion, creed, gender (including pregnancy status), sexual orientation, gender identity (which includes transgender and other gender non-conforming individuals), gender expression, hair expression, marital status, parental status, age, national origin, ancestry, disability, medical condition, genetic information, veteran or military status, citizenship status, or any other characteristic protected (herein referred to as “protected characteristics”) by applicable federal, state, or local laws. Equal employment opportunity will be extended in all aspects of the employer-employee relationship, including, but not limited to, recruitment, hiring, training, promotion, transfer, demotion, compensation, benefits, layoff, and termination. In addition, Gallagher will make reasonable accommodations to known physical or mental limitations of an otherwise qualified person with a disability, unless the accommodation would impose an undue hardship on the operation of our business.

Search firms, consulting firms, or individuals who submit unsolicited resumes acknowledge that those resumes are available for Gallagher's consideration without any obligation to pay finder/referral fees. Gallagher, or any of its subsidiaries, will only pay a fee for a successful candidate placement when there is an agreement in place with the providing entity and the candidate submission complies with the regional guidelines for such submissions.

Gallagher never extends an offer of employment or requests any personal identification information without having received an online application and conducted one or more in-person or video interviews. We also do not use Skype, Zoom, Telegram or Gmail as part of our hiring process. If you have received any communication referencing the offer of a job at Gallagher and you have not submitted an online application or been interviewed by a Gallagher employee, please do not assume that the offer is being sent from a legitimate Gallagher representative.

© 2026 Arthur J. Gallagher & Co. All Rights Reserved.