Kyle Shonak serves as Gordon Brothers’ chief transaction officer for North America, leading strategy and cross-functional collaboration to maximize asset value. With nearly 25 years of experience in growth and wind-down transactions, he works with management teams, private equity sponsors and asset-based lenders to provide capital and guidance in high-stakes situations.
Much of Shonak’s career has centered on special assets and workouts, beginning during the 2007–2009 financial crisis. Since then, he’s led engagements with distressed borrowers across asset classes, often playing a lead or fulcrum role. These situations have demanded creativity and the ability to navigate complexity with third-party partners to deliver the best possible outcomes.
Shonak’s back-end experience has taught him what makes or breaks a deal. In a recent transaction with Big Lots, Shonak leveraged Gordon Brothers’ full platform — capital, store closings, inventory procurement, brand management and real estate — to preserve going-concern value in bankruptcy. By structuring a flexible bid, he adapted quickly to shifting conditions under tight deadlines.
Shonak is clear-eyed about the nature of dealmaking: “Time is not your friend; it will kill a deal. The only certainty is change, and no deal is a straight line.” He builds flexible deal structures that account for competing interests and potential disconnects — whether personal, organizational or external.
Shonak has seen companies face liquidation because of a “that can’t be done” mindset. For him, that phrase is fuel to push forward. Dealmaking, he believes, is a practice refined through repetition. Each deal — win or lose — offers insight.
Shonak’s advice to future rainmakers is direct: expect the unexpected and trust yourself. The toughest deals often bring the most growth. Even failed deals are valuable, because what you learn shapes how you win the next one.
