Form 4: PegaSystems COO/CFO Stillwell Increases Stake

Kenneth Stillwell, COO and CFO of Pegasystems Inc., reported a net increase in his direct beneficial ownership of common stock following option exercises, RSU conversions, and subsequent sales for tax and personal reasons.

Summary

• Kenneth Stillwell, COO and CFO of Pegasystems Inc., reported multiple transactions involving the company's common stock on December 5, 2025, and December 7, 2025.
• Transactions included the exercise of stock options and conversion of Restricted Stock Units (RSUs) into common stock.
• A total of 58,864 shares were acquired through these exercises and conversions.
• Simultaneously, 39,621 shares were disposed of to cover tax withholding obligations related to the vesting of equity awards.
• An additional 14,405 shares were sold in the open market at weighted average prices ranging from $57.70 to $57.89.
• Following these transactions, Stillwell's direct beneficial ownership of Pegasystems common stock increased by a net of 4,838 shares, from an initial 129,950 shares to 134,788 shares.

Sentiment

Score: 7

Explanation: The net increase in beneficial ownership by a key executive is generally positive, indicating confidence in the company's future. However, the substantial sales for tax and other reasons temper the overall positive sentiment.

Positives

• A net increase of 4,838 shares in direct beneficial ownership by a key executive (COO, CFO) signals continued confidence in Pegasystems Inc.
• The successful vesting of 20,000 performance-based stock options for the fiscal year ended December 31, 2024, indicates the company met specific performance criteria.

Negatives

• Significant sales of 14,405 shares in the open market, in addition to shares withheld for taxes, represent a partial monetization of holdings by a key executive.

Future Outlook

The remaining 75% of certain Restricted Stock Units (RSUs) are scheduled to vest in equal quarterly amounts over the next 3 years from their respective exercisable dates. Additionally, up to 75% of the 80,000 share option granted on March 5, 2024, is expected to vest on the second anniversary of the grant date (March 5, 2026), contingent upon Pegasystems' satisfaction of specific performance criteria for the fiscal year ended December 31, 2025.

Industry Context

This Form 4 filing details specific insider trading activity for Pegasystems Inc. and does not provide broader industry context or trends. It is a company-specific disclosure of executive stock transactions.

Stakeholder Impact

• Shareholders may view the net increase in insider ownership as a positive signal of management's confidence in the company's prospects.
• The sales of shares, even if for tax purposes, could be scrutinized by investors looking for signs of executive sentiment regarding future stock performance.

Next Steps

• Continued vesting of remaining Restricted Stock Units (RSUs) in equal quarterly amounts over the next 3 years.
• Potential vesting of up to 75% of the 80,000 share option on March 5, 2026, based on Pegasystems' performance criteria for fiscal year 2025.

Key Dates

Keywords

Pegasystems, PEGA, Insider Trading, Form 4, Stock Options, RSU, Kenneth Stillwell, Beneficial Ownership, Executive Transactions, COO, CFO