Progress Software Stock Down 36%. Learn Why, If AI Makes $PGRS A Buy

Core Viewpoint - Progress Software's stock has dropped 36% in 2025 despite consistently beating expectations and raising guidance, raising questions about whether the stock is undervalued [2] Company Overview - Progress Software, based in Burlington, Massachusetts, has a growth strategy focused on acquisitions, primarily targeting small database and business software companies [3] - The company employs 3,000 people and serves 86,000 customers, generating approximately $250 million in revenue in the third quarter, with an average revenue per customer of $3,000 [4] Legal Challenges - A significant uncertainty for Progress's future is a lawsuit stemming from a breach in its MOVEit file transfer app, potentially exposing the personal data of 95.8 million individuals across 2,773 organizations [5] - The financial liability from the legal proceedings could range from $30 million to over $500 million, depending on the outcome [6] Bull Case - The bullish perspective on Progress Software is supported by its high margins, low valuation (8x earnings), and strong recurring revenue growth (47%) [7] - Successful integration of the ShareFile acquisition and plans to reduce debt by $160 million this year could improve operations [8] - The company's AI capabilities are expected to enhance pricing power and customer acquisition, potentially leading to faster growth [8] Customer Value Proposition - Progress Software provides AI-driven solutions to help small businesses improve productivity and customer satisfaction, boasting a satisfaction rate of 93% to 94% [10] - The company enables clients to utilize generative AI for marketing and operational efficiencies, allowing faster response times and improved service delivery [12] Bear Case - Approximately 12% of Progress shares are sold short, indicating bearish sentiment among investors [15] - High debt levels, totaling over $1.9 billion, and risks associated with acquisitions could negatively impact earnings [16] - Weak organic growth and competitive challenges in various product categories raise concerns about the company's ability to sustain revenue growth [16] - Questions regarding the quality of earnings have emerged, particularly with a decline in GAAP operating margins from 25% in Q3 2024 to 18% in Q3 2025 [16]