$GWRE

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.

Original reporting
SEC EDGAR · King James Winston
Published Sep 21, 2026, 9:23 PM UTC
Analysis
AlphAI AI DeskAI-generated
Added to AlphAI Sep 21, 2026, 10:00 PM UTC. Informational, not investment advice.
How this was made
AlphAI summarizes source reporting and applies a structured AI analysis for relevance, timing, sentiment and ticker impact. Always verify material claims with the original publisher.
AlphAI market briefInsider activity
Primary signal
$GWRE
Bearish
medium confidence
Mentioned
$GWRE
Relevance
5/10
AlphAI data visualization · based on SEC EDGAR
Decision brief

The 30-second read

$GWREBearishLow
01

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.

02

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.

03

What to watch

The 10b5‑1 plan may have been pre‑set before any material news, limiting interpretive value.

Relevance 5/10Novelty 6/10Timing: filing today (2026‑09‑21)

Background

SEC Form 4 filings disclose insider transactions and are primary sources for such events.

Company-level read

Ticker impact

$GWREBearishMedium confidence
Context

Chief Admin Officer sold 13,195 shares for $1.9M via a 10b5‑1 plan, reducing his stake to 44,558 shares.

Expected impact

Potential modest downside pressure over the next few days.

Evidence & confidence

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

  • Guidewire Software, Inc.

    Provider of core system software for the insurance industry, ticker GWRE.

  • King James Winston

    Chief Administrative Officer of Guidewire, reporting the sale.

Full insider trading history

This story covers one filing. See everything behind it: every insider buy and sell on record, 10b5-1 plans, late filings, and which officers and directors are trading.

Related articles

$GWREMedAI 8/10

Guidewire's Cash Flow and Buybacks: Can Both Keep Scaling?

Guidewire Software (GWRE) reported fiscal 2026 operating cash flow of $390M, up 30% YoY, and repurchased $606M in shares. Non-GAAP operating income rose 63% to $340M. For fiscal 2027, it projects $445M-$465M in operating cash flow. Competitors ServiceNow (NOW) and Salesforce (CRM) also reported strong cash flows and buyback plans.

$GWREHighAI 8/10

Guidewire Software’s Cloud Shift Powers Earnings Call

Guidewire Software (GWRE) reported Q4 earnings with record ARR of $1.242B, up 19% YoY. Cloud ARR grew 35% and now represents 84% of total ARR. Subscription revenue surged 37% to $916M. Total revenue reached $1.475B, up 23%. The company expects fiscal 2027 ARR of $1.45B-$1.46B and total revenue of $1.707B-$1.727B.

$GWREMed

Guidewire climbs as investors focus on cloud growth, recurring revenue, and bullish analyst support

Guidewire Software (GWRE) rose 8.6% today, driven by investor confidence in its cloud transition and recurring revenue growth. Fiscal 2026 revenue increased 23%, with subscription revenue up 33%. Annual recurring revenue reached $1.24B, with 19% growth. Analysts raised price targets, including one to $235. Insiders sold shares, while hedge funds showed mixed activity.

$GWRELow

Guidewire Software (GWRE) Following Earnings And 2027 Guidance Is The Valuation Case Changing

Guidewire Software (GWRE) reported Q4 and FY2026 earnings, providing 2027 revenue and operating income guidance. Shares closed at $140.92, down 24.9% YTD but up 53.9% over 3 years. The company's valuation is debated, with a fair value estimate of $210.86, though its P/E ratio of 84.2x is high compared to peers. Growth potential is tied to cloud-based systems and global expansion, but risks include large deal delays and foreign exchange impacts.

$GWREHighAI 8/10

Guidewire (GWRE) Q4 2026 Earnings Call Transcript

Guidewire (GWRE) reported Q4 2026 earnings with ARR growth of 19% YoY to $1.242B, total revenue up 23% to $1.475B, and non-GAAP operating income up 63% to $340M. Cloud ARR grew 35% YoY, comprising 84% of total ARR. The company guided FY 2027 ARR to $1.45B-$1.46B, up 18% at midpoint. Subscription revenue rose 37% YoY to $916M, while license revenue declined 7% to $235M. Management highlighted record-low attrition rates and strong adoption of AI-driven products like ProNavigator and PricingCenter.