CEO Accelerator Program

Program Overview:
Kingsway Financial Services (NYSE:KFS), a publicly traded holding company, is seeking early-in-career managers and entrepreneurs interested in entrepreneurship through acquisition (ETA) to join the CEO Accelerator Program. Those hired will join the Kingsway team in the Chicago area to begin the process of launching a search to acquire and subsequently operate their own businesses. After an initial training period, Kingsway will provide aid, oversight, and capital as our searchers source opportunities, evaluate potential deals, and acquire a business. Upon acquisition, searchers will step in as the CEO of the business–building out their team, setting and executing the strategic vision, and growing their equity stake in the business.

Life as Kingsway Searcher:
Throughout the entire process, specialists within Kingsway are available to support you with everything from sourcing your first deal to solving an HR issue at the business you acquire (and everything in between). Once you have closed your transaction, you will begin your management career. We will help you deploy the Kingsway Business System of setting and executing strategy, including regular calls with CEO Accelerator Program advisors, weekly calls Kingsway’s CEO, and monthly board meetings with your directors.

We have designed the CEO Accelerator Program to be a supportive environment for entrepreneurs to pursue their goals and achieve their vision within the broader architecture of a growing, long-term oriented public holding company. This program is a key strategic initiative for us, and new hires will be integral members of the larger Kingsway team.

Searcher Qualifications:
There is no specific work background necessary for an entrepreneur to be successful in this role. We are more interested in who you are, what drives you, and what you want to do with your career. We encourage any applicants interested in small business ownership and entrepreneurship to apply regardless of experience. Applicants should submit a cover letter with their resume briefly explaining why they want to pursue this opportunity and what makes this form of entrepreneurship right for them.

New hires will receive competitive compensation and benefits as well as equity in the business they acquire. They will also be eligible for student loan repayment matching from Kingsway (up to certain limits), transaction bonuses, and stock plan participation at the public company level.

To Apply:
If interested, please submit your resume and a cover letter to

This is a rolling application process and Kingsway will continue to accept applications and review candidates starting in until the program has reached its capacity for this year.

Contact Information:

J.T. Fitzgerald, CEO, Kingsway Financial Services