Operator-in-Residence

Kingsway (NYSE: KWY), the only publicly traded US Company employing the Search Fund model to acquire and build great businesses, recently held its 2026 Investor Day at the New York Stock Exchange. Included attached is the presentation shared with our Investors detailing how the Kingsway Search Xcelerator has grown from Vision to Tangible Proof over the last several years as we have successfully executed on both new platform and add-on acquisitions. We are now seeking to expand our team of Operator-in-Residence roles. Applications (including Resume and Cover Letter) should be submitted to redacted The Kingsway Search Xcelerator (KSX) platform invests in talented entrepreneurs who source, acquire, and manage their own businesses within Kingsway’s holding company structure as CEO. At Kingsway, we wholly believe that the success of a business begins with strong focus on its people and a set of shared values. We typically look to partner with OIRs who have several years of post-graduate work experience. OIR responsibilities within the KSX program include: •Participate in weekly team check ins to learn from your peers •Apply KSX’s data driven learnings to identify & screen industries of interest •Learn the basics and best practices of sourcing transactions enabled by KSX tools •Actively engage with business owners to originate proprietary deal flow •Evaluate intermediated opportunities with support from Kingsway Business Development •Negotiate transaction terms and letter of intent with support from Kingsway Legal & advisers •Lead due diligence efforts with support of functional specialists (Legal, HR, Finance, etc) •Close transaction & transition to CEO role Qualifications •Employee must be curious, have an entrepreneurial drive, must be process oriented, humble and have a high degree of integrity. •Ethical and transparent behavior in dealing with sensitive information and handling business relationships. •Extraordinary business and people management skills with the ability to not only identify opportunities but also enroll others to deliver the desired results. •Excellent communication and negotiation skills to interact with stakeholders, potential sellers, and industry professionals. •Strong financial acumen with the ability to analyze financial statements and investment opportunities. •Understanding of leverage and complex capital structures; knowledge of junior capital(subordinated debt and equity) markets required •Demonstrated ability to work independently, manage multiple projects, and meet tight deadlines. •Bachelor's degree and MBA or related graduate degree is required. •Demonstrated interest in operational leadership, entrepreneurship, private equity, or related field. •Willingness to relocate to the location of acquired business. •Must be authorized to work in U.S. (permanent residency with permanent work authorization).