Progress Software Corporation: A Challenging Investment Profile with Leverage and Inconsistent Performance

Progress Software Corporation presents a challenging investment profile with leverage, inconsistent performance, and overreliance on acquisitions to drive growth. Trading at 8x P/E and 8x EBITDA, the company has delivered flat returns over the past five years. Recent acquisitions, such as ShareFile from Citrix, have pushed leverage above 3.5x and created difficult comps. Organic growth remains weak and lumpy, and adjusted free cash flow metrics obscure the company's financial position. With a looming comp from the ShareFile acquisition and potential headwinds, a strategic sale to a value-tech acquiror remains a potential upside.