SEC EDGARSEP 211 min read$GWRE

Rosenbaum Michael George sold $10.6M of GWRE

Rosenbaum Michael George (Chief Executive Officer) sold 73,490 shares of Guidewire Software, Inc. (GWRE) at an average of $144.50 ($144.47–$145.92, $10.62M total) across 2 trades over 2026-09-17 to 2026-09-21 under a Rule 10b5-1 trading plan.

Original reporting

SEC EDGAR · Rosenbaum Michael George

Published Sep 21, 2026, 9:22 PM UTC

Analysis

AlphAI AI DeskAI-generated

Added to AlphAI Sep 21, 2026, 9:59 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.

About AlphAI AI Desk Scoring methodology Report an issue

AlphAI market briefInsider activity

Primary signal

$GWRE

Bearish

medium confidence

Mentioned

$GWRE

Relevance

6/10

AlphAI data visualization · based on SEC EDGAR

Decision brief

The 30-second read

$GWREBearishMed

Why it matters

The sale reduces insider ownership and may affect market perception of management confidence.

Market read

Primary disclosure of a sizable insider sell; relevant for traders monitoring insider activity.

What to watch

Potential upcoming earnings or strategic moves not disclosed yet.

Relevance 6/10Novelty 8/10Timing: after‑hours filing on Sep 21

Background

SEC Form 4 filing discloses insider transactions; the CEO used a pre‑arranged 10b5‑1 plan.

Company-level read

Ticker impact

AI estimates · verify against primary disclosures

$GWREBearishMedium confidence

Context

CEO Michael George Rosenbaum sold 73,490 shares for $10.6M via a 10b5‑1 plan, reducing his stake to 279,666 shares.

Expected impact

Potential short‑term downward pressure on GWRE stock.

Evidence & confidence

Large $10M sale by the top executive is material, but no accompanying corporate event suggests limited immediate impact.

Market effects

Sector

May prompt scrutiny of other software‑sector insiders.

Regional

Limited to US equity markets where GWRE trades.

Global

Low; impact confined to GWRE investors.

Counterpoint

What could challenge this read

Insider sell could be routine liquidity management, not a bearish signal.

Key entities

Company
Guidewire Software, Inc.
Provider of core system software for the property‑and‑casualty insurance industry.
Executive
Michael George Rosenbaum
Chief Executive Officer of Guidewire.

Read at source ← All news

OCT 2

$GWREMed

DA Davidson reiterates Guidewire stock Buy rating on new customer win

DA Davidson reiterated a Buy rating and $222 price target for Guidewire Software (NYSE:GWRE), citing a new major customer win. The target implies 42% upside from the current price. Guidewire reported 23% revenue growth over the last year and exceeded Q4 earnings expectations. The stock has declined 23% year-to-date.

investing.com2 min

SEP 29

$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.

zacks.com3 min

SEP 16

$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.

tipranks.com3 min

SEP 14

$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.

quiverquant.com2 min

SEP 12

$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.

simplywall.st3 min

SEP 9