Tracked deals
4
4 tracked deals across 2022-2025.
Chicago, Illinois, United States
Kingsway Financial Services (“Kingsway”) is a publicly traded holding company (NYSE: KFS) that acquires and operates asset-light, recurring revenue services businesses using a decentralized operator/search-fund style model (including exposure across extended warranty and other business services).
Tracked deals
4
4 tracked deals across 2022-2025.
Recent pace
0
0 tracked deals announced in the last 12 months.
Deal mix
Addon
2 addon · 2 buyout
Last 3 years
Supporting Data
Kingsway Financial Services (via its Kingsway Skilled Trades platform) acquired AAA Flexible Pipe Cleaning Corporation (doing business as Advanced Plumbing and Drain) from the Fisco family, closing on August 1, 2025. The acquisition adds plumbing, sewer cleaning and waterproofing capabilities and municipal/commercial/residential end-market exposure to Kingsway's skilled-trades services portfolio.
Kingsway Financial Services acquired Roundhouse Electric & Equipment Co., Inc., a provider of mission-critical field maintenance and motor repair services to midstream natural gas pipeline operators and utilities in the Permian Basin; the transaction closed July 1, 2025. Generational Capital Markets advised the sellers, and Kingsway said Roundhouse is a strategic fit for its Kingsway Search Xcelerator platform to expand its portfolio of asset-light, recurring-revenue services businesses.
Kingsway Financial Services (NYSE: KFS) acquired Digital Diagnostics Imaging, Inc. (DDI), a New Jersey-based provider of outsourced cardiac monitoring telemetry services, for $11.0 million in an all-cash transaction funded with cash and debt. The acquisition, completed under Kingsway's Search Xcelerator platform, is immediately accretive and adds about $4.2 million of annual revenue and $1.8 million of annual adjusted EBITDA while bringing a capital-light, recurring-revenue capability into Kingsway's portfolio.
Kingsway Financial Services (NYSE: KFS) acquired Secure Nursing Service, Inc. (SNS), a Los Angeles-based provider of per diem and travel nursing and allied healthcare staffing. The asset purchase was financed with cash on hand and a term loan from Signature Bank; SNS adds $19.7 million of unaudited revenue and $2.7 million of unaudited adjusted EBITDA and is expected to be immediately accretive.
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