Jolee Crosby | Swiss Re

Jolee Crosby, CEO of Canada & English Caribbean Reinsurance and Canada Country President, Swiss Re

Jolee Crosby often jokes she’s a ‘recovering attorney,’ but she’s quick to assert she deliberately chose insurance as a career.

She grew up in Kansas City and was the first in her family to graduate from college — with a law degree from the University of Missouri. While working as a litigator, she got her first glimpse into the world of insurance.

“I started to see insurance makes the world go round,” Crosby says, recalling a conversation with a woman who worked as in-house counsel at State Farm at the time, a conversation that profoundly influenced her. “Insurance is where the decisions are made, and the fundamental impact of insurance on society just spoke to me,” she says.

Crosby joined Swiss Re in 1998, embarking on a journey that took her across continents and various roles within the company. She worked both on the property and casualty (direct and reinsurance) and life and health sides, eventually leading her to her current position as of summer last year.

“Today, I pinch myself that I went from the first person in my family to graduate college to where I am now, here in Toronto, working in this role, with this team, and this market. I am so grateful,” she says.

She didn’t originally see herself as a CEO, but she credits her rise to the C-suite to others’ encouragement and belief in her potential. She credits these people for challenging the notion that women must choose between family and a career.

“When I first started in the industry, for the first six years or so, I worked part-time as a mom of three,” she recalls. “I would often be approached to be a team leader. But I had told myself that you’re either on the mommy track, or you’re on the leadership track.

“That’s a false choice that women sometimes think we must make. My career is proof of that.”

Crosby soon got interested in leadership, realizing that was a way for her to have more of an impact on people around her.

She considers herself a servant leader, emphasizing her commitment to fostering growth and excellence within her team.

“I’m a change agent but I really care about the people around me,” as she describes herself. “I like to feel connected to my team and help them be the best they can be and have a fulfilling career. I want to provide them with the tools they need and help them up our game so we can deliver for our industry and our customers.”

Addressing the challenges women face in their senior leadership ambitions, Crosby points out the tendency towards self-censorship and the fear of failure that often prevent women from achieving success. She shares a defining moment in her career where, against a leader’s advice and her own doubts, she volunteered for a high-stakes project, a decision that catalyzed her confidence and expanded her professional network.

“It really is all in your mindset: always find a way to say yes. Don’t let fear dictate your life choices,” Crosby says.

On making the P&C industry more accessible for women aspiring to senior leadership, Crosby commends the strides made in Canada, noting the higher representation of female leaders compared to other markets.

“In general, however, so few senior leadership roles exist, it will always be competitive. When you’re the candidate, and especially a woman, we have to think about what differentiates us from everyone else and use that to our advantage,” Crosby says.

She advocates for an industry more receptive to varied leadership styles and approaches. “A diverse team of individuals fosters diversity of thought, and helps us meet the needs of all the customer segments we’re responsible for serving.”