Profile
Whitney Benson is an insurance industry leader with nearly two decades of experience and the co-founder, COO, and CTO of CaptiveSimple, a Canadian and US-based insurtech platform expanding access to captive insurance. She helps brokers and business owners turn insurance from a fixed, opaque expense into a strategic asset that retains capital in local communities and supports collaboration across the captive life cycle.
Passionate about advancing women in business and leadership, Benson believes careers are not ladders to climb but rivers to navigate – sometimes calm, sometimes turbulent, always in motion. Through education, mentorship, and example, she encourages women to see where they are today as an achievement shaped by resilience, responsibility, and courage.
Benson created and teaches Captives 101, a CE-approved course in Alberta, and has delivered education nationally through the Insurance Institute of Canada and internationally through the CaptiveSimple platform and live training. She will speak at the 2026 IBAA Convention on captives and alternative risk strategies.
Her leadership has been recognized through GenNext 40 under 40 and as a finalist for Emerging Business Person of the Year. She also champions initiatives, including Paramount’s #30years30charities, Central Alberta Brokers Day, and Dress for Success Central Alberta. She lives and works in Alberta.
4711 Yonge St, North York, ON M2N 7E4
403 550 8524
whitney@victurus.co
linkedin.com/in/whitneybenson
captivesimple.com
Whitney Benson
Founder, Chief Operating Officer, and Chief Technology Officer
CaptiveSimple
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Bio
Milestones
Profile
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Special Report
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Bio
Milestones
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Special Report
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Bio
Milestones
2006–2023
2014–2017
2015–2024
2025
Present
Insurance Adviser at Paramount Insurance
2006–2023
Bookkeeper at Paramount Insurance
2014–2017
Chief Operations Officer and Marketing Director at Paramount Insurance
2015–2024
GenNext 40 under 40
2025
Figurehead and Community Engagement Leader at Paramount Insurance since 2024
Founder, Chief Operating Officer, and Chief Technology Officer at CaptiveSimple since 2024
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