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Kingsway Financial Services Inc., through its subsidiaries, engages in the extended warranty and business services in the United States. The company operates through two segments, Extended Warranty and Kingsway Search Xcelerator. The Extended Warranty segment markets, sells, and administers vehicle service agreements and related products for new and used automobiles, motorcycles, and ATVs. This segment also markets and distributes warranty products to manufacturers, distributors, and installers of heating, ventilation and air conditioning, standby generator, commercial LED lighting, and commercial refrigeration equipment; and provides equipment breakdown and maintenance support services to companies, as well as after-market vehicle protection services. The Kingsway Search Xcelerator offers outsourced finance and human resources consulting services, including operational accounting, such as bookkeeping, accounting, financial reporting, and analysis and strategic finance services; technical accounting comprising initial public offerings, Securities and Exchange Commission reporting, and international consolidation services; human resources, workforce management, and compliance support services; and advisory services. This segment also provides financial executive services for project and interim staffing engagements; search services for permanent placements; healthcare staffing services to acute healthcare facilities for short-term and day-to-day needs of hospitals; software products for the management needs of all types of shared-ownership properties; and fully managed outsourced cardiac telemetry services, as well as provides mobile monitors to the hospitals. The company offers its products and services through credit unions and dealers. Kingsway Financial Services Inc. was incorporated in 1989 and is headquartered in Chicago, Illinois.

Metromile, Inc. provides insurance policies for automobile owners in the United States. It operates through two segments, Insurance Services and Enterprise Business Solutions. The company offers pay-per-mile auto insurance policies. It also provides The Pulse, a device that plugs into the diagnostic port of its customer's car and transmits data, such as miles driven, driving habits, phone use, speeding, hard braking, accelerating, cornering, and location over wireless cellular networks. In addition, the company offers access to its technology under software as a service arrangement, as well as professional services to third-party customers. Metromile, Inc. was founded in 2011 and is headquartered in San Francisco, California.

Root, Inc. provides insurance products and services in the United States. The company offers automobile, homeowners, and renters insurance products. It operates a direct-to-consumer model; and serves customers primarily through mobile applications, as well as through its website. The company's direct distribution channels also cover digital, media, and referral channels, as well as distribution partners and agencies. Root, Inc. was incorporated in 2015 and is headquartered in Columbus, Ohio.

Trean Insurance Group, Inc. underwrites specialty casualty insurance products in the United States. The company underwrites business, predominantly workers' compensation, accident and health, and medical professional liability products. It also offers a variety of services, including issuing carrier, claims administration, and reinsurance brokerage services. The company offers its products through program partners and managing general agents. Trean Insurance Group, Inc. was founded in 1996 and is based in Wayzata, Minnesota.