Knowledge Corner

Jill Garrity didn’t aspire to work in the insurance industry, however her time here has shaped it.

Her introduction came through family. Both of her parents worked in the industry and helped her get started. What began as an entry point eventually became a career spanning more than three decades, a milestone she admits still surprises her.

“Like many others, I didn’t grow up thinking, ‘I’m going into insurance,’” she says. “I’ve been in the industry for over three decades now, which feels strange to say. The time went by so fast.”

About fifteen years ago, Jill faced a pivotal career moment: transitioning from Personal Lines to Wrap Administration. What began as a challenge became a defining chapter.

“At the time, I had no experience with Wrap programs or Commercial Insurance in general, so it truly felt like starting over in a completely new arena,” she said. “What began as a big challenge ultimately became the most rewarding career, working for TSIB.”

Even after more than three decades in the industry, Jill remains motivated by growth. Her experience is a reminder that growth often requires stepping into unfamiliar territory, even after years of experience. 

“I enjoy the challenge. Insurance coverage, projects and clients all change. There’s always something new to analyze and solve,” she says. “It sounds cliché, but I still learn something new every day.”

Measuring Success by Others’ Growth
When Jill began her career, women were far less visible in leadership roles. Over the years, she has seen meaningful progress across the industry. She believes continued progress depends on intentional mentorship and development. A belief reflected in the advice she offers to young women entering the field.

“Encourage a culture that supports women in leadership positions,” she notes. “Provide mentorship and leadership development programs,” she advises. “Never underestimate yourself. Ask questions. Work for a company that aligns with your values.”

What helped her most, she explains, was preparation and consistency, knowing the material and building credibility over time. She learned an important lesson early on:

“You don’t have to change who you are to succeed. Strength isn’t always being the loudest person in the room.”

That philosophy would come to define her leadership style as steady, thoughtful, and relationship driven. When asked about her biggest achievement, Jill doesn’t mention a title or milestone. For her, success is measured in the growth of others.

“It has been rewarding to see people I’ve hired and coached over the years step into leadership roles.”

Family as Foundation
If she had to describe herself in one word, Jill said “Family.” That perspective shapes how she balances life and work.

“Who I am is defined by both of my families — at home and at TSIB,” she shared. “Work-life balance has always been important to me,” she says. “It’s not perfect, and it shifts at times when work demands more, and times when my personal life takes priority.”

She encourages her teams to prioritize balance as well, understanding that long-term success requires sustainability. Her husband has played a pivotal role in her journey both personally and professionally. His support gave her the confidence to take risks and step into new opportunities.

“He taught me about construction, knowledge that was needed for my job working in Wrap Administration,” she shares. “More importantly, he has always been my biggest supporter.”

Looking Ahead
Looking ahead, Jill’s goals are not centered on personal advancement, but on the impact she can leave behind. Rather than focusing on titles or accolades, she is driven by the opportunity to strengthen the people around her and build something lasting within the organization.

“I’d love to leave behind a strong, confident team with real opportunities ahead of them.”

At TSIB, she has found a culture that closely aligns with that vision. One that values collaboration, accountability, and long-term relationships over short-term wins.

“There is a real commitment to both colleagues and clients and to doing the right thing.”

From family influence to trusted mentor, Jill’s career reflects consistency and quiet leadership. Her story is a reminder that legacy is not built overnight and is shaped through relationships, mentorship, and a commitment to lifting others along the way.

This article is part of our Women’s History Month spotlight lineup. Don’t miss any of the other inspiring stories highlighted in this series!