Form 4: Pegasystems COO/CFO Stillwell Exercises Options, Sells Shares

Pegasystems COO and CFO Kenneth Stillwell exercised stock options and subsequently sold a portion of the acquired shares on October 24, 2025.

Summary

• Kenneth Stillwell, COO and CFO of Pegasystems Inc. (PEGA), reported transactions involving the company's common stock and stock options.
• On October 24, 2025, Stillwell exercised options to acquire 52,828 shares of common stock at an exercise price of $31.05 per share.
• Concurrently, 35,657 shares were disposed of at $66.91 per share to cover tax liabilities or the exercise price.
• An additional 17,171 shares were sold on the open market at a weighted average price of $66.40 per share, with prices ranging from $66.37 to $66.60.
• Following these transactions, Stillwell's direct beneficial ownership of common stock is 127,826 shares.
• The remaining beneficial ownership of derivative stock options is 88,044.
• The exercised options had an original vesting schedule of 25% on March 5, 2025, with the remaining 75% vesting in equal quarterly installments over the subsequent three years, and an expiration date of March 5, 2034.

Sentiment

Score: 5

Explanation: The filing reports a routine insider transaction involving the exercise of stock options and subsequent sale of shares, which is a common event for executives. It does not inherently indicate strong positive or negative sentiment towards the company's operational performance, but rather a personal financial decision.

Positives

• The exercise of stock options at a significantly lower price ($31.05) compared to the market sale price (average $66.40 $66.91) indicates a substantial personal gain for the executive, reflecting positively on the company's stock performance since the options were granted.
• The company's stock price being well above the option exercise price suggests a healthy valuation and growth over the option's life.

Negatives

• The sale of 17,171 shares on the open market by a key executive, even after accounting for tax-related dispositions, represents a reduction in direct beneficial ownership and could be perceived by some investors as a signal, though it is a common practice for executives to diversify or realize gains.

Future Outlook

This filing does not contain any forward-looking statements or guidance regarding the company's future performance or outlook.

Industry Context

This insider transaction is a routine event related to executive compensation and does not directly reflect broader industry trends. However, the executive's decision to exercise options and sell shares is a common practice in the technology and software industry for executives to realize gains and manage personal finances.

Stakeholder Impact

• Shareholders: May interpret the sale of shares by a key executive as a signal, potentially influencing short-term trading sentiment, although it's a common practice for tax and diversification purposes.
• Employees: No direct impact mentioned.

Key Dates

Recommendation

This Form 4 filing details a routine executive compensation event where the COO/CFO exercised stock options and subsequently sold a portion of the acquired shares. While the exercise indicates a personal gain for the executive due to the stock's appreciation, the net sale of shares, even for tax purposes, might be viewed with slight caution by some investors. It does not provide new fundamental information about the company's operations or future prospects that would warrant a strong 'buy' or 'sell' recommendation based solely on this filing. Therefore, a 'hold' recommendation is appropriate, suggesting investors maintain their current position while awaiting further operational updates.

Keywords

Pegasystems, PEGA, Insider Transaction, Form 4, Stock Options, Executive Compensation, Share Sale, COO, CFO