Anna McCrindell | Wawanesa Mutual Insurance

Anna McCrindell, Senior Vice President, Chief Operating Officer (East), Wawanesa Mutual Insurance

A campus recruiter was the P&C industry entry point for Anna McCrindell, senior vice president and chief operating officer (East) at Wawanesa Mutual Insurance.

“A recession was starting, and I jumped into a commercial underwriter training program with an American company,” she said. “Good training is essential, so that’s something I look back at and say, ‘Wow, I was lucky.’”

As someone who likes a challenge and thrives on change, she noted that when she joined the industry back in 1990, not a lot of change was taking place. “I decided to go for career coaching because I wanted to establish ‘Am I in the right place?’” McCrindell said.

“My career counselor pointed out other things I could be good at. It was pivotal because it made me look at my work in insurance differently. It made me ask myself ‘How can I chart my path?’ I started to work on an MBA and got a tap on the shoulder by a leader who recognized my motivation. That started my path to leadership as a commercial lines manager and then an SVP.”

Her career’s also benefitted from great mentors.

“One leader I still talk to taught me about the value of collaborating,” she said. “He was a strong believer in diversity, gathering a group of people with different perspectives to tackle problems. In the underwriting world, we can be kind of rigid, and he would always be creative. I took away the notion that small improvements over time can really drive big change.”

Plus, it’s important to stay open to continual learning. “I will be in a role and feel like I’ve accomplished and learned all that I can, so that’s when I’m looking for that next opportunity,” she said.

The other key piece is connecting with people and asking for help; reaching out to those who are succeeding and learning from them about how they did it.

“You need a lot of courage to ask someone to be your mentor,” McCrindell said. “But what I have noticed is how gracious people are, and how much they want to help and are happy to talk to you and share experiences. I have a few people who have sought me out. I approach them by asking what they want to get out of the relationship and assess whether I have what they need. It’s important to establish what we want to achieve together in our conversations.”

It’s also important to be building a workforce that’s diverse and open, and creating places where people feel they can come to work and contribute.

“A company needs to be clear on its employee value proposition,” she said. “New grads coming into this industry need to know about training programs, how they’ll be supported, career pathing, succession planning. They want to know, ‘How have others gone before me and what can I expect?’”

Applicants should understand when they’re interviewing that it’s not just the company interviewing you, McCrindell added. “They’re also interviewing the company and want to have the experience of, ‘Wow, I like these people. I could really work here.’ Every decision I’ve made to take on a role has been about the people who work there because I want to be a part of that team.”