PRGS PROGRESS SOFTWARE CORP /MA Insider Trading

PRGS Director Gawlick Rainer bought 1,710 shares at $43.48; stock down 34.0% from 52-week high, currently $46.11

Gawlick Rainer purchased 1,710 shares of PROGRESS SOFTWARE CORP /MA at $43.48, bringing his holdings to 55,544 shares. The transaction occurred when the stock was trading 34.0% below its 52-week high of $69.89 and has declined 26.4% over the past 90 days. The company has a P/E of 34.41 against a $2.0B market cap, with recent quarterly revenue of $237,400,000 and 8.5% annual growth. This represents the director's first discretionary open-market purchase on record across all tickers tracked. While the purchase coincides with significant price weakness, the company maintains positive earnings and steady revenue growth.

Director David Krall buys 5,125 shares of PRGS at $48.90; stock now down 28.5% from 52-week high.

Director David Krall purchased 5,125 shares of Progress Software at $48.90 on 2025-07-23, increasing his holdings by 5.4% to 100,090 shares. The transaction occurs at a price 28.5% below the 52-week high of $69.89 and follows a 22.6% decline over the prior 30 days. Krall has one prior open-market purchase on record with an average 90-day return of +6.3%, though his cross-ticker track record shows a 0% 90-day win rate. His single prior trade at Progress Software was a sale on 2024-04-11 that resulted in a +4.6% 90-day return—a poorly-timed exit from the insider's perspective as the stock rose after the sale. The absolute size of this purchase is modest relative to his existing 95,000-share position, and the stock's current valuation (P/E 37.29) remains elevated despite recent weakness.

CEO Yogesh K Gupta bought 2,100 shares of PRGS at $49.14 as stock is -28.5% from 52-week high

Gupta purchased 2,100 shares (2.1K shares) at $49.14, bringing his holdings to 232,396 shares (232.4K shares). The purchase occurs during significant downward pressure: the stock trades at $49.97, down -28.5% from its 52-week high of $69.89 and -22.6% over the past 30 days. At the same-ticker level, Gupta's prior 5 trades at PRGS comprise 5 separate sales occurring between February and October 2024, of which only 1 of 3 measurable sales proved well-timed at the 90-day mark. His cross-ticker track record shows 5 prior sells with a 90-day well-timed rate of 33.33%, indicating inconsistent timing overall. The shift from five prior sales to this discretionary purchase is notable, though the company remains fundamentally sound with $237,355,000 (237.4M) in quarterly revenue, +8.5% annual growth, and a market cap of $2,154,124,099.59 (2.2B).

EVP Jarrett Loren sold 34,093 shares at $61.10 across 3 separate sales for $2.1M, reducing holdings 74.4%.

Jarrett Loren, EVP/GM Digital Experience, executed 3 separate open-market sales totaling 34,093 shares for $2,083,082.30 at a blended average price of $61.10 on 2025-05-09, reducing his holdings from 45,840 to 11,747 shares (a -74.4% reduction in stake). The sale price of $61.10 was 2.3% below the current price of $62.52 and 12.5% below the 52-week high of $69.89; the stock has appreciated 8.4% over the prior 30 days and 9.5% over 90 days. His prior 3 sales at PRGS (all on 2023-04-20) showed positive 30-day and 90-day returns, with a 0% well-timed rate at the 90-day mark across same-ticker history. The large proportional reduction in equity stake and multiple transaction structure warrant observation of subsequent company developments and stock price action relative to sector trends.

CFO Anthony Folger sells 15,000 PRGS shares in 3 transactions for $844,555.70; holdings reduced 25.2%

Anthony Folger, Chief Financial Officer of Progress Software, executed three separate sales on 2025-02-03 totaling 15,000 shares for $844,555.70, reducing his holdings from 59,564 shares to 44,564 shares—a 25.2% reduction in pre-transaction holdings. The blended average price of $56.30 is approximately 1.8% below the current price of $57.33, and the stock is down 12.2% over the past 30 days and down 18.0% from its 52-week high of $69.89. Across his cross-ticker open-market history, Folger's 6 prior sells have demonstrated a 100.00% well-timed rate at the 90-day mark (avg 90d return -7.6%), and at PRGS specifically, his 2 measurable prior sells in 2024 both posted negative 90-day returns (-7.3% and -7.9%). However, without a disclosed 10b5-1 trading plan FLAG or transaction reason, the motivation for this sizable reduction cannot be determined from the filing alone.

CFO Anthony Folger sells 7,797 shares at $67.38–$67.87 for $525,420.70, reducing holdings 18.8%

Anthony Folger, Chief Financial Officer of Progress Software, executed two separate sales on 2024-10-16, selling 7,797 shares (7.8K shares) for a blended average price of $67.39, bringing his post-transaction holdings to 33,774 shares (33.8K shares) from 41,571 shares (41.6K shares). The sale represents an 18.8% reduction in his shareholding at prices near the 52-week high of $67.37. While the stock has appreciated 14.6% over the past 30 days and 18.7% over 90 days, placing the company's valuation metrics at a notably elevated P/E of 34.15, his prior four sales at this ticker show no yet-measurable outcomes. The scale of this divestiture—nearly a fifth of holdings—is material relative to his normal transaction size, though his cross-ticker track record shows only four prior open-market sells across all tickers.

CEO Gupta sells 8,028 shares of PRGS at $67.00; stock up 17.7% in 90 days post-sale

On 2024-10-01, Chief Executive Officer Yogesh K Gupta sold 8,028 shares at $67.00 for $537,916.14, reducing his holdings by 5.1%. This transaction occurred near the 52-week high of $67.37, with the stock subsequently trading at $64.81 today. Gupta's cross-ticker track record shows 4 prior sells with an average 90-day return of -4.9% and a well-timed rate of 50.00%, but his ticker-specific history at PRGS (4 prior sells) shows mixed results: 2 of 4 prior sells were well-timed at the 90-day mark, with 90-day returns of -11.8%, -13.0%, +3.4%, and +1.7%. The current sale occurred as PRGS stock has gained 17.7% over 90 days and 11.4% over 30 days, and at a valuation of 37.90 P/E supported by 15.4% annual revenue growth and $175.1M in latest-quarter revenue. The sale at or near the 52-week high, coupled with the subsequent 90-day positive performance, represents a poorly-timed exit relative to recent momentum; this contrasts with Gupta's mixed historical success timing exits in this stock.