Pamela Derksen | Insurance Brokers Association of Ontario (IBAO)

Pamela Derksen, Incoming President, Insurance Brokers Association of Ontario (IBAO

Even experienced leaders sometimes question their confidence, says Pamela Derksen, incoming president of the IBAO.

“I still remember my first day in a new leadership role, sitting in my office, my heart pounding. I told myself it would be the hardest day I’d have in that job,” she tells Canadian Underwriter.

A mentor later offered a simple reminder: “You know this topic better than anyone in the room.”

More than two decades into her insurance career, Derksen still returns to that moment.

“Confidence isn’t about knowing everything. It’s about trusting your experience and your ability to find answers when you don’t have them,” she says.

Unexpected start

Derksen began exploring career opportunities after completing a BA in economics and political science at the University of Calgary during a challenging job market for new graduates. A professor connected her with Royal Insurance’s trainee program.

“I didn’t land that opportunity, but I was offered a position as an underwriting assistant. That turned out to be a great break,” Derksen says.

She’s since built a career across the insurance sector, holding senior leadership roles in commercial underwriting, operations, and product development before moving to the broker side in 2018 and into compliance leadership in 2022. Today, she’s the deputy chief compliance officer at NFP Canada, overseeing compliance, privacy and regulatory initiatives across property and casualty, life and benefits. She’ll be stepping into the role of IBAO President in April.

Looking back, Derksen describes her insurance journey as both unexpected and rewarding. But the breadth of opportunities is one of the biggest reasons she stayed in the industry.

“One of the best parts of insurance is exposure to so many industries,” she says. “You gain insight into your clients’ businesses, apply what you learn, and ultimately help them succeed, too.”

Mentors are key

Mentorship has played an important role throughout Derksen’s career. “One mentor in particular helped me develop my personal brand, become more self-aware, and advocated for me when opportunities came up,” she says. “I’ve also learned from mentors who emphasized the importance of developing sales skills. No matter your role, you’re always selling ideas and building buy-in.”

Her earliest mentor was much closer to home.

“My father consistently built my confidence and believed in me wholeheartedly,” she says. “He used to say: ‘I’m so glad I had you, and not a son.’ That early message shaped how I saw myself and gave me the confidence to pursue opportunities throughout my career.”

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Say, ‘Yes’

While insurance offers real opportunities for growth, Derksen believes the industry must remain intentional about removing barriers to attract and retain women.

“A lack of flexibility, outdated work environments, or situations where women’s input isn’t valued can make it harder for women to stay and progress,” she says. “On the brokerage side, it’s important to avoid the perception that sales roles are for men and service roles are for women. Modern workplaces recognize that acquiring, servicing, and retaining customers is a team effort.”

Derksen encourages women entering the industry to build their networks early, stay curious, keep learning, and be willing to say, ‘Yes,’ to opportunities that feel like a stretch.

“Say, ‘Yes,’ to opportunities you’re not completely sure you’re ready for,” she says. “Trust yourself to figure it out.”