Finding My Fit: From Intern to Sales Enablement at Gallagher

I still remember what my experience looked like before Gallagher, flipping omelets in a dining hall at the University of Iowa. So, when I joined Gallagher as a sales intern in the summer of 2022, it was my first real exposure to both corporate America and sales. I came in with a lot of curiosity and excitement about what lay ahead.

I genuinely enjoyed my internship, and after graduating, I joined full time as a Sales Associate in the fall of 2023. While the transition felt natural in some ways, it also came with a learning curve. Over time, I began to struggle with the technical aspects of the role, and that started to affect my confidence particularly when it came to prospecting.

That was when I began to question whether I was in the right role.

Recognizing the Need for Change

I had always been encouraged to pursue a career in sales, so I started with high expectations for myself. However, as I became more involved in cold calling, I realized how challenging it was for me personally. As someone who values positive interactions, the constant rejection began to impact my confidence.

There came a point where I noticed I wasn’t showing up as my usual self. That realization, although difficult, prompted me to reflect more honestly on where my strengths truly lay.

With the support of my mentor, I explored a move into account management to better understand the client side of the business. In that role, I enjoyed building relationships, but I also missed the creative aspect of my work. At that stage, I felt uncertain, I had explored two roles and still hadn’t quite found the right fit.”

Exploring Opportunities Within Gallagher

When I started thinking about my next step, I briefly looked at opportunities outside Gallagher. However, nothing quite compared to the culture, flexibility, and growth opportunities I had experienced here. That made my decision clear to continue exploring within the organization.

I began networking internally and connected with around 15 colleagues across different teams. I approached each conversation with a set of consistent questions around career paths, day to day responsibilities, required skills, advice, and potential opportunities.

Even when those conversations didn’t lead directly to a role, they were incredibly valuable. I came away with new perspectives, stronger connections, and a clearer understanding of where I might fit.

Finding the Right Fit in Sales Enablement

Through this process, I connected with the Early Talent team, who introduced me to Caitlin Connors. Through her, I learnt more about sales enablement, a role I had heard of but hadn’t fully understood before.

Caitlin then connected me with Emily Brainard, and after several conversations, job shadowing sessions, and interviews, I began to see how this role could bring together many of my strengths. Sales enablement combines relationship building, strategic thinking, and creativity, something that resonated strongly with me.

Creativity has always been a big part of who I am, whether through painting, designing, or building something from scratch. Being able to bring that into my work, while still partnering closely with sales teams, felt both natural and motivating.

In August 2025, I formally moved into the Sales Enablement team. Since then, I’ve been able to contribute more confidently, collaborate across teams, and help bring ideas to life. All while working alongside colleagues I already understood and enjoyed partnering with."

Growth Through Every Experience

Looking back, each role I explored played an important part in preparing me for where I am today.

My time in sales helped me understand what producers need, how presentations are structured, what resonates, and how to support successful outcomes. Account management gave me a deeper understanding of Gallagher’s resources and how we deliver value to clients.

Even when I felt unsure, I was building experience that would later prove essential. Those moments weren’t setbacks; they were part of the process of growth."

One of the biggest reasons I chose to stay at Gallagher throughout this journey was the culture. I’ve had mentors, colleagues, and leaders who took the time to guide me, support me, and help me navigate uncertainty. That willingness to invest in people even early in their careers says a lot about the environment here.

A Perspective for Those Still Figuring It Out

If there’s one thing I’ve learned, it’s that it’s completely okay not to have everything figured out early in your career.

My advice would be to stay open, step outside your comfort zone, and prioritize building connections. Those conversations can open doors you hadn’t considered and help you better understand what aligns with your strengths.

We spend a significant amount of our lives working and it’s worth finding something that genuinely motivates you. And often, getting there involves exploring different paths before finding the one that feels right.