King James Winston sold $1.9M of GWRE
King James Winston (Chief Admin Officer, Gen Couns) sold 13,195 shares of Guidewire Software, Inc. (GWRE) at an average of $144.52 ($144.47–$144.98, $1.91M total) across 2 trades over 2026-09-17 to 2026-09-18 under a Rule 10b5-1 trading plan.
How this was made
The 30-second read
Why it matters
The disclosed sale reduces insider ownership and may be interpreted as a negative sentiment cue, though the pre‑arranged nature tempers the signal.
Market read
An insider sale of $1.9 M by a senior officer is noteworthy for GWRE shareholders and may prompt short‑term price scrutiny.
What to watch
The 10b5‑1 plan may have been pre‑set before any material news, limiting interpretive value.
Background
SEC Form 4 filings disclose insider transactions and are primary sources for such events.
Ticker impact
Chief Admin Officer sold 13,195 shares for $1.9M via a 10b5‑1 plan, reducing his stake to 44,558 shares.
Potential modest downside pressure over the next few days.
Officer-level insider sales of ~2 M dollars are material enough to attract attention, especially when executed through a pre‑arranged plan.
Market effects
Minimal; the sale does not affect the broader software sector.
None; the filing is U.S. specific.
Low; only relevant to GWRE investors.
Counterpoint
The sale could be routine portfolio rebalancing, not a bearish signal.
Key entities
- CompanyGuidewire Software, Inc.
Provider of core system software for the insurance industry, ticker GWRE.
- InsiderKing James Winston
Chief Administrative Officer of Guidewire, reporting the sale.



