Operator-in-Residence

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February 19, 2026

by a searcher from Harvard University - Harvard Business School in Greenwich, CT, USA

Kingsway Financial Services Inc. (“Kingsway”) (NYSE: KFS) is the only publicly-traded US company employing the Search Fund model to acquire and build great businesses. Kingsway owns and operates a collection of high-quality B2B and B2C services companies that are asset-light, growing, profitable, and that have recurring revenues. Kingsway seeks to compound long-term shareholder value on a per share basis via its decentralized management model, its talented team of operators, and its tax-advantaged corporate structure. Kingsway Search Xcelerator (KSX) seeks to add multiple Operator-in-Residence (OIR) roles to search, acquire, and operate U.S. based small businesses in partnership with Kingsway. Responsibilities OIR responsibilities within the KSX Program include: Industry Research: Apply KSX's data driven learnings to identify & screen industries of interest Sourcing & Outreach: Actively engage with business owners and deal intermediaries to originate deal flow using the basics and best practices of sourcing transactions, enabled by KSX tools Due Diligence: Lead due diligence efforts with support of functional specialists (Legal, HR, Finance, etc.) Negotiation: Lead negotiation of transaction terms and letter of intent with support from Kingsway Qualifications Kingsway is seeking candidates with the following qualifications: Work Experience: We look to partner with OIRs who have several years of post-graduate work experience (3+ years out of business school or equivalent) Core Values: Qualified applicants must be able to demonstrate a focus on continuous improvement, supported by intellectual curiosity and a high degree of both integrity and humility. Management Skills: Exceptional business and people management skills with the ability to not only identify opportunities but also build consensus among a team and deliver desired results. Communication: Excellent communication and negotiation skills necessary to interact with stakeholders, potential sellers, and industry professionals. Financial Acumen: Ability to analyze financial statements and investment opportunities (LBO modeling, Capital structure, etc.) Education: Bachelor's degree and MBA or related graduate degree is required Entrepreneurial Drive: Demonstrated ability to work independently, manage multiple projects and meet tight deadlines. Geography: Must be authorized to work in U.S. (permanent residency with work authorization) and willing to relocate to the location of the acquired business.
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Reply by a searcher
in Ellensburg, WA, USA
^redacted‌ - Are you able to share any compensation or pay band information on this? Here in WA state, this is now a requirement, and folks have grown accustomed to at least knowing a range expected...
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Reply by a searcher
from Louisiana State University in Nashville, TN, USA
Thank you ^redacted‌ for the tag. Would love to learn more, Charles. I will send you a DM. My email is also redacted and cell is###-###-####
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