Profile
“Our mission is simple: we empower financial planners to spend more time building trust, deepening client relationships, and growing their business”
Chris Arthur, Bold Wealth
Jonathan Weekes is president, Canada at BOXX Insurance and a recognized authority in commercial insurance, with a particular focus on professional liability and cyber. With nearly 20 years of industry experience, he brings deep expertise at the intersection of insurance, cyber risk, and technology.
Since stepping into the role in early 2025, Weekes has helped drive BOXX’s momentum in the Canadian market, reinforcing its position as a homegrown leader in all-in-one cyber insurance solutions and protection services for brokers, MGAs, and affinity partners. Before joining BOXX, he served as SVP, cyber practice leader at HUB International, and previously held key roles at Aon, AIG, and progressive leadership positions at Marsh.
Weekes is Certified in Risk and Information Systems Control (CRISC) by ISACA, underscoring his commitment to staying at the leading edge of cyber and risk management standards. He is also a regular commentator in leading industry and business publications, including The Financial Post, Canadian Underwriter, Insurance Business, and others, where he shares insights on emerging cyber risks and the evolving insurance landscape.
302 Bay St., Suite 703-01
613 903 7479
sarah.madden@boxxinsurance.com
linkedin.com/in/jonathanm-weekes
boxxinsurance.com
Jonathan Weekes
President, Canada
BOXX Insurance
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“Whether I’m in a strategy session or a hiring meeting, I try to lead with understanding. Financial planners are under immense pressure, and so are our internal teams. The best way to earn trust is to truly listen”
Chris Arthur,
Bold Wealth
2009
2017
2021
2022
2025
Moved from personal lines insurance into commercial lines broking with Aon and established a Technology Errors & Omissions underwriting facility with Lloyd’s to underwrite E&O and cyber risk
2009
Changed paths and moved to AIG to underwrite large, complex E&O and cyber risks
2017
Appointed Cyber Growth Leader after two years at Marsh Canada
2021
Appointed National Cyber Practice Leader at HUB International
2022
Appointed President of BOXX Insurance, an all-in-one cyber insurance and protection provider based in Toronto
2025
Assistant Vice President and Senior Broker at MJ Hall & Company since 2018
Present
Milestones
