Michael George Rosenbaum, chief executive officer of Guidewire Software (GWRE), has filed 74 Form 4 transactions across two companies, with every dollar moving in one direction: sales. The total sell value is $25,026,095.78, and there are no open-market purchases, no acquisitions, and no buy-side activity of any kind in the record. The pattern is uniform. His recent filings show 22 sales in a row, all in GWRE, spaced roughly weekly from late April through mid-September 2026.
The sales are consistent in size but not trivial. Individual GWRE transactions range from $126,804 on June 22 to $692,271.69 on June 16, with most falling between $150,000 and $250,000. The cadence is steady: a sale every seven days, sometimes two in a week, as seen on June 15 and June 16. The largest single transaction in the recent window is the June 16 sale, which is more than three times the typical weekly amount. There is no clustering around any particular date or price level that would suggest a reaction to a specific event.
Rosenbaum also holds a position in DocuSign (DOCU), but the filings there are option exercises (code M) with a value of zero, dated September 3 and June 3, 2026. Those are mechanical events, not sales, and they produce no cash. The only compensation event in the recent record is a GWRE grant (code A) on September 11, also valued at zero. The direction is unambiguous: Rosenbaum has been a consistent seller of GWRE stock through open-market transactions, with no offsetting purchases in either company.
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