Profile
Anna McCrindell will close a 35-year insurance career in May 2026 at a defining moment, having led Wawanesa Insurance’s Commercial team past $1 billion in gross written premium in 2025 and overseen its transition to a nationally led operating model.
Named to Insurance Business Canada’s Elite Women 2026 list, she retires as senior vice president and chief commercial lines officer with a record defined by strategic thinking, execution, and sustained contribution to Canada’s commercial sector.
Her career was never perfectly mapped out. It evolved through intention, opportunity, and a willingness to step forward when mentors saw potential she had not yet recognized in herself. “My career has been shaped by a blend of intention and opportunity and a belief that growth often happens when you step into the unknown,” she says. She built her path by delivering consistently, earning trust, and following work that challenged her and aligned with her values.
That mindset defined her leadership at Wawanesa. The company is working to become a more competitive and profitable mutual insurer, focused on delivering tangible benefits to members and communities. Moving from regionally led operations to a national structure at the start of 2026 required leading large-scale transformation without sacrificing performance.
Commercial insurance itself continues to evolve, demanding modernization while brokers, members, and teams expect responsiveness and discipline in underwriting. McCrindell addressed that tension by setting priorities and decision paths that allowed teams to move forward without losing focus on fundamentals.
She describes her greatest achievement as establishing herself as a respected leader in Canadian commercial insurance, trusted for judgment and delivery. Over three decades, she influenced underwriting standards, product innovation, and leadership development across global and Canadian organizations.
Public recognition, including being twice named by IBC as a leading female figure and now earning Elite Women 2026 honours, affirms the scope of that impact.
Her effectiveness rests on an ability to communicate and translate strategy into action. Colleagues know her for balancing technical expertise with a people-first approach and for leading with integrity and transparency, especially when decisions carry weight.
McCrindell served on the board of the Institute for Catastrophic Loss Reduction and as a governor and chair of the Academic Council for the Insurance Institute of Canada. An FCIP and CRM, she also earned the top student FCIP award, underscoring the technical depth that anchored her leadership.
McCrindell’s rise unfolded at a time when few women occupied senior underwriting or executive roles. Advancement pathways were limited, and balancing ambition with personal responsibilities required persistence within systems not built for dual demands.
In her view, recognition as an Elite Woman carries responsibility. “Representation matters and seeing women in senior leadership roles helps others visualize what’s possible for them,” she says.
McCrindell’s legacy reaches across the commercial organizations she strengthened and the leadership conversations she helped advance. In partnership with the Insurance Institute’s South Western Chapter, she created a national Women in Leadership seminar series designed to spark honest dialogue about how leadership is developed and how a future rooted in impact, integrity, and courage can be sustained.
At home, her two adult children have chosen careers in insurance, a sign that the industry she served remains worth investing in.
770 Main St, PO Box 160, Moncton, NB E1C 0G1
1 800 455 7337
communication@assomption.ca
linkedin.com/in/anna-mccrindell-9851b016
wawanesa.com
Anna McCrindell
Senior Vice President and Chief Commercial Lines Officer
Wawanesa Insurance
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Bio
Milestones
Profile
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Bio
Milestones
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Special Report
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Bio
Milestones
2019
2020
2023
2026
Present
Recipient of IBC’s Steamatic Canada Award for Women of Distinction
2019
Joined Wawanesa as Vice President, Commercial Insurance
Recognized as one of IBC’s Elite Women
2020
Promoted to Wawanesa’s Executive Leadership Team
2023
Retiring following a remarkable 35-year insurance career
2026
CEO at HIROC since 2017
Present
Milestones
Milestones
Sept 2021
Feb 2022
Apr 2022
Jul 2022
Aug
2022
Suncorp Bank introduces Solar Home Bonus offer for customers who are choosing renewable energy for their homes
Sept 2021
Month-on-month market share growth commences
Feb 2022
Suncorp Bank wins the Canstar award for most outstanding value in investment loans
Apr 2022
Suncorp Bank wins Money Magazine’s Bank of the Year and Business Bank of the Year awards for the fifth year in a row
Jul 2022
Suncorp Bank’s turnaround times are the lowest they have ever been. The lender becomes Australia’s first certified carbon neutral bank for both its operation and transaction services
Aug 2022
Milestones
As a founding member of WOW! (Women. Opportunity. Winning.), an employee resource group created for all women of Ryan Specialty, Phillips Topping has long championed for women in the industry.
“It’s very important to set an example and to not only inspire but mentor other females,” she adds.
In addition to her sharp marketing eye, the key to Phillips Topping’s success lies in her high-energy approach and positive attitude.
“As the leader of a team, it’s important to motivate and encourage your team members. People work very hard and do their best and it’s important to recognize these efforts. For my career overall, my attitude has been one of curiosity. The more you can learn, the better you’ll understand the business, and then the deeper your knowledge will become, making you a better team member.”
Chief underwriting officer of executive risk at Chubb
President of financial insurance solutions at Kemper
Chief underwriting officer at Axis Capital
CEO of global Insurance at Endurance
CEO of global Insurance at Sompo International
Empathy underpins that discipline. Prickett has struggled in the industry. She has felt what it is like when promised support does not materialize. Having worked across almost every function in the company, she understands operational detail and the pressure agents face. That shared experience shapes her leadership.
Structural barriers also shaped her path. As a woman and a mother, she encountered the assumption that serious business building required keeping priorities “out of order for a time.” She also experienced the double standard that frames firm women as difficult while praising similar behaviour in men.
“If you have a choice between being liked and doing the right thing, doing the right thing is always better, even if it’s the unpopular thing,” Prickett says.
She wants to dismantle the expectation that women must choose between career and family, or between strength and kindness. In her view, leadership demands both conviction and care.
Being named an Elite Woman carries weight. Prickett did not have female role models in the industry when she started. She hopes visibility changes that. “I hope I can be an example. Not of perfection, but of persistence. Of building from your values and staying true to who you are.”
The legacy Prickett is still defining centres on proof – proof that a large, profitable company can grow without sacrificing integrity; proof that agents can build real assets while keeping their priorities intact; and proof that leadership does not require abandoning who you are to succeed.
“If you have a choice between being liked and doing the right thing, doing the right thing is always better, even if it’s the unpopular thing”
Lee-Ann Prickett,
Experior Financial Group
“What I’ve learned is that when you build from your values, when you put people first, when you do the right thing even when it’s hard, that becomes your plan”
Lee-Ann Prickett,
Experior Financial Group
“I’ve always believed that if you love what you do, you’ll never settle, and that attitude has guided every decision I’ve made”
Danny Ibrahim,
KeyRate Mortgage
“My strongest professional quality is my ability to build trust and long-term relationships, whether with clients, colleagues, or stakeholders”
Danny Ibrahim,
KeyRate Mortgage
“My strongest professional quality is my ability to build trust and long-term relationships, whether with clients, colleagues, or stakeholders”
Danny Ibrahim,
KeyRate Mortgage
“I’ve always believed that if you love what you do, you’ll never settle, and that attitude has guided every decision I’ve made”
Danny Ibrahim,
KeyRate Mortgage