Kenneth Stillwell, chief operating officer and chief financial officer of Pegasystems (PEGA), has filed 79 Form 4 transactions with the SEC, all in that single company. The pattern is one-sided. His total sell value across those filings is $6,422,678.28, and his total buy value is zero. He has not made an open-market purchase in the period covered by the filings, and the three most recent trades are all tax withholding events, not discretionary sales.
The recent activity is dominated by option exercises paired with automatic share withholdings. On September 7, 2026, Stillwell exercised options valued at $0 and had shares withheld to cover taxes worth $76,774.80. Similar paired filings occurred on September 5, September 4, and September 1, with withholding values of $64,744.88, $47,979.84, and $34,049.25. The largest single withholding came on August 10, 2026, at $602,355.56, following an option exercise valued at $439,344. These F-code transactions are mechanical, triggered by vesting or exercise, and do not reflect a decision to sell.
The discretionary open-market sales are fewer but larger. On March 10, 2026, Stillwell sold $1,971,640 worth of PEGA stock. On May 5, 2026, he sold $305,560.35 and had $636,943.84 withheld for taxes after an exercise worth $439,344. A smaller sale of $43,170 appeared on April 1, 2026. The most recent open-market sale was May 5, 2026. Since then, every trade has been an M-F pair with no cash proceeds. The data shows a COO and CFO who sells periodically, but whose current activity is limited to the administrative mechanics of equity compensation.
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