SiriusPoint : Digital Trucking Broker LuckyTruck and SiriusPoint Announce Strategic Partnership

The investment will enable LuckyTruck to grow its platform across the US

New York, NY, December 14, 2021 - LuckyTruck, Corp. ("LuckyTruck"), a digital broker and aggregator specializing in commercial trucking insurance, and SiriusPoint Ltd. ("SiriusPoint") (NYSE: SPNT), a global specialty insurer and reinsurer, today announced a strategic partnership which will see SiriusPoint invest in and partner with the specialist trucking broker.

LuckyTruck is a niche broker and aggregator that makes the purchase of insurance for trucking fleets in the United States more transparent, customized, affordable, and convenient. The company aims to disrupt commercial trucking insurance brokerage, offering an alternative to slow, difficult, paper-heavy processes. LuckyTruck offers truckers a range of insurance products specifically tailored to their needs and a transaction can be completed online in minutes, rather than the weeks it has historically taken to secure insurance.

SiriusPoint's partnership with LuckyTruck will generate insights and understanding into the evolution and behavior of the small commercial trucking segment, and create opportunity for the companies to develop insurance products in the space. LuckyTruck aims to continue its expansion of business operations across the US, through adding new licensing, expanding the company's talented producer base, solidifying new partnerships with key members of the ecosystem (e.g., MGA's, Carriers and Trucking Groups) and building out its specialized trucking digital distribution platform.

"We welcome LuckyTruck to our growing portfolio of partnerships focused on driving disruptive change in the Insurance industry" said Patrick Charles, Head of Americas P&C at SiriusPoint. "We are excited to partner with LuckyTruck to accelerate innovation in the commercial trucking insurance space. Our strategic partnership is an opportunity to drive change where it's needed, to improve insurance coverage and customer experience in an underserved and growing area of the US business insurance market."

CEO and Founder of LuckyTruck, Devin Bostick, added: "Commercial trucking is undergoing a fundamental shift. There's a heavy infusion of capital in this area, that translates to a vibrant and growing logistics ecosystem. At LuckyTruck, we are excited to strategically partner with SiriusPoint and enable small fleets to experience a truly world class risk management experience."

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About LuckyTruck

LuckyTruck is a digital provider of trucking insurance intended to make the purchasing process more transparent, customized, affordable, and convenient for small trucking fleets. The company allows users to get personalized advice, compare trucking quotes & insurance online, enabling them to make well-informed decisions tailored specifically for trucking companies. LuckyTruck's platform allows for automatic review and approval during its streamlined application process, which takes a matter of minutes as opposed to weeks. For more information, please visitwww.Luckytruck.co.

About SiriusPoint

SiriusPoint Ltd. (SiriusPoint) is a global insurer and reinsurer providing solutions to clients and brokers in almost 150 countries. Bermuda-headquartered with offices around the world, we are listed on the New York Stock Exchange (SPNT). We write a global portfolio of Accident and Health, Specialty, Property and Runoff, combining data and creative thinking to underwrite risks with skill and discipline. With over $3 billion total capital, SiriusPoint's operating companies have a financial strength rating of A- (Excellent) from AM Best, S&P and Fitch. For more information, please visit www.siriuspt.com.

SiriusPoint Forward-Looking Statements

We make statements in this report that are forward-looking statements within the meaning of the U.S. federal securities laws including the companies' ability to generate insights and understanding into the evolution and behavior of the small commercial trucking segment, and to create opportunities for the companies to develop new insurance products in the space. We intend these forward-looking statements to be covered by the safe harbor provisions for forward-looking statements in the U.S. Federal securities laws. These statements involve risks and uncertainties that could cause actual results to differ materially from those contained in forward-looking statements made on behalf of SiriusPoint. These risks and uncertainties include the impact of general economic conditions and conditions affecting the insurance and reinsurance industry, the adequacy of our reserves, fluctuation in the results of operations; pandemic or other catastrophic event, such as the ongoing COVID-19 outbreak; uncertainty of success in investing in early-stage companies, such as the risk of loss of an initial investment, highly variable returns on investments, delay in receiving return on investment, difficulty in liquidating the investment; the costs, expense and difficulties of the integration of the operations of Third Point Reinsurance Ltd. and Sirius International Insurance Group, Ltd.; our ability to assess underwriting risk, trends in rates for property and casualty insurance and reinsurance, competition, investment market and investment income fluctuations, trends in insured and paid losses, regulatory and legal uncertainties and other risk factors described in SiriusPoint's Quarterly Reports on Form 10-Q for the periods ended March 31, 2021 and June 30, 2021. Except as required by applicable law or regulation, we disclaim any obligation to publicly update or revise any forward-looking statement to reflect changes in underlying assumptions or factors, or new information, data or methods, future events or other circumstances after the date of this report.

Contacts

LuckyTruck
Devin Bostick
Founder | CEO
[email protected]

SiriusPoint, Investor Relations
Clare Kerrigan
[email protected]
[phone]

SiriusPoint, Media
Sarah Hills, Rein4ce
[email protected]
[phone]