Operator-in-Residence
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.
in Ellensburg, WA, USA
from Louisiana State University in Nashville, TN, USA