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

Pegasystems Inc.'s COO and CFO, Kenneth Stillwell, exercised stock options and subsequently sold a portion of the acquired shares and additional shares on November 3, 2025.

Summary

• Kenneth Stillwell, COO and CFO of Pegasystems Inc. (PEGA), engaged in multiple transactions on November 3, 2025.
• Exercised 25,920 stock options at an exercise price of $16.95 per share.
• Disposed of 14,478 shares of common stock at $62.29 per share for tax withholding purposes.
• Sold an additional 11,442 shares of common stock at a weighted average price of $62.18 per share.
• Following these transactions, Stillwell beneficially owns 127,826 shares of common stock directly and 103,680 derivative securities (stock options).
• The sale price for the 11,442 shares ranged from $62.07 to $62.31.
• The transactions were made pursuant to a Rule 10b5-1(c) plan, indicating a pre-arranged trading strategy.

Sentiment

Score: 6

Explanation: Neutral to slightly positive. While an insider sold shares, it was part of a pre-planned exercise-and-sell strategy (10b5-1 plan), which is a common and expected event for executives managing their equity compensation. The significant gain from option exercise is positive for the executive, but the reduction in direct ownership is a minor negative.

Positives

• The transactions were executed under a Rule 10b5-1(c) plan, indicating pre-planned sales and reducing concerns about opportunistic insider selling.
• The exercise of options at a significantly lower price ($16.95) compared to the sale price (around $62) indicates a substantial gain for the insider.

Negatives

• An insider sale, even if pre-planned, reduces the direct ownership stake of a key executive in the company.

Future Outlook

NA

Industry Context

NA

Stakeholder Impact

• Shareholders: Minor dilution from option exercise, but the overall impact is minimal as it's a routine insider transaction. The sale reduces the insider's direct stake, which some investors might view neutrally or slightly negatively.
• Employees: No direct impact mentioned.

Key Dates

Recommendation

The filing details routine insider transactions by a key executive (COO, CFO) involving the exercise of stock options and subsequent sale of shares, primarily for tax withholding and portfolio diversification, under a pre-arranged 10b5-1 plan. Such transactions are common and do not typically signal a change in the company's fundamental outlook or performance. The insider still retains a significant number of shares and options. Therefore, the filing itself does not provide new information warranting a change in investment thesis; a 'hold' recommendation is appropriate, pending further operational or financial updates from Pegasystems.

Keywords

Pegasystems, PEGA, Kenneth Stillwell, Insider Trading, Form 4, Stock Options, Share Sale, COO, CFO, Beneficial Ownership, Rule 10b5-1