In this episode, I interview Lindsey DiGangi, Vice President of Field Operations and Marketing at Pennsylvania Lumberman's Mutual Insurance Company to talk about her leadership journey and what it really looks like to grow a career from the inside out. Lindsey shared how a single risk management class in college sparked her interest in insurance, which eventually led her to an internship and then a 12-year career spanning field operations, marketing, process improvement, and customer relationships. We talked about the creativity required to make complex insurance topics resonate, how gaining diverse perspectives across an organization shapes better solutions, and why meaningful projects and strong support matter so much when developing interns and early-career talent.

Lindsey also offered honest insights about career growth in smaller organizations, where progress may feel slower but often comes with deeper experience and broader exposure. She points out that titles matter far less than the skills you build along the way, and that saying yes to unexpected opportunities can open doors you didn’t even know existed. We also discuss employee engagement, lateral mobility, and her vision for creating a more equitable playing field in insurance through accessible entry points and upskilling opportunities.