March
7

From the Mailroom to the Boardroom: Jenna's Journey as an Elite Woman in Insurance

When Jenna Terry is your colleague, it’s impossible not to feel inspired by her energy and work ethic. Throughout her career, she has built a reputation as a leader who embraces change, fosters collaboration, and drives innovation. Born and raised in Edmonton, she began her journey in the insurance industry in 1992 as a summer temporary employee at Pafco Insurance, working in the mailroom and covering the switchboard while deciding on her next steps. By the end of that summer, she was offered a role as an Underwriting Assistant – an opportunity that would shape the course of her professional life.

Over the next few years, she gained valuable experience at Pafco before joining Peace Hills Insurance in 1996. After a brief career break to focus on raising her four children, she returned to Peace Hills in 2004 and steadily progressed through a variety of roles. From Personal Lines Underwriter to Corporate Underwriting Manager and later Regional Director, she played a key role in developing underwriting strategies and implementing internal systems that streamlined our business operations.

Today, as the Director of Business Integration at the helm of our Guidewire implementation project, Jenna is responsible for ensuring our new system meets the needs of every stakeholder. She leads advisory meetings, gathers critical feedback, and collaborates closely with executives and project managers to drive the project forward. “This is a large and complex transition,” she says. “But having the opportunity to help shape the future of our operations and improve the experience for both our staff and broker partners makes the work incredibly rewarding.”

Her leadership and expertise have not gone unnoticed. Joyce Cassie, our ROC Business Development Advisor, used to report to Jenna when she was a Regional Director and nominated her for the Insurance Business Canada’s Elite Women awards.

"When I saw the nominations open up, I immediately thought of Jenna. She is so dedicated to her job and the company and will go out of her way to make things happen."

Beyond technical expertise, Joyce values Jenna for her ability to mentor and support those around her, which leaves a lasting impression on those around her.

"She was always a very understanding boss and leader, consistently taking the time to listen, understand, and explain. Jenna’s knowledge of insurance and the industry is insurmountable, and she utilizes this knowledge to the full extent— she is one of the smartest people I know."

Throughout her career, Jenna has navigated both personal and professional obstacles. Balancing a leadership role while raising four children required flexibility and dedication: two important values here at Peace Hills. But one of the aspects about the insurance industry that kept her going and one she continues to appreciate most is its diversity and ongoing evolution. “There are always new opportunities to grow, whether through technology, strategy, or building strong relationships,” she notes. “This industry is dynamic, and that’s what makes it exciting.”

Back in 2008 she played a significant role in our last underwriting management system launch, “GIMS”—an experience that provided valuable insights as she now leads another major system implementation. “Every transformation initiative comes with its challenges,” she explains. “But learning from previous projects and identifying areas for improvement has been key in making this implementation as successful as possible.”

When discussing the importance of recognizing women in the insurance industry - especially on the eve of International Women's Day - she is passionate about the message it sends to the next generation. “Honoring women in leadership helps showcase the wealth of opportunity in this field,” she explains. “It’s important for young professionals to see what’s possible and to feel encouraged to contribute their ideas and expertise.”

For those beginning their careers, her advice is simple: embrace every opportunity to learn. “The insurance industry needs fresh talent, new ideas, and innovative thinking,” she says. “There is so much potential for growth, and those who are willing to learn will find tremendous opportunities.” There is something for everyone, and everyone has something to offer.

From her early days in the mailroom to her current leadership role, Jenna’s career reflects a commitment to growth, innovation, and mentorship. Her contributions at Peace Hills will undoubtedly leave a lasting impression, and we are incredibly proud to have her on our team. Today, we are thrilled to celebrate her well-deserved recognition as an Elite Woman in Insurance by Insurance Business Canada. Congratulations, Jenna!

You can red the entire IBC Elite Women 2025 article here.