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Insider · CIK 0001586253

James Winston King

officer

Files at GWRE (Guidewire Software, Inc.). First filing Dec 19, 2024, latest Sep 21, 2026.

James Winston King files SEC Form 4 as officer at GWRE (Guidewire Software, Inc.). Since Dec 19, 2024, James Winston King has reported 0 open-market buys worth $0 and 13 open-market sells worth $8.9M, the latest filed on Sep 21, 2026.

A track record needs three past buys with six months of prices behind them; James Winston King has 0, so none is measured yet.

The newest scored trade: sold $1.9M of GWRE on Sep 17, 2026, filed Sep 21, 2026, scored 40 (moderate), under a 10b5-1 plan. In the last 12 months: 0 buys worth $0 and 5 sells worth $3.1M.

Track record
Not enough history
Fewer than three past buys with six months of prices.
Median 6-month excess
-
after past buys, n = 0
Hit rate
-
past buys that beat the index over 6 months
Open-market trades
0 / 13
$0 bought, $8.9M sold

Where the trades landed

Last year at the company this insider has traded most, with each buy and sell on the bar it happened.

GWRE: Guidewire Software, Inc.

GWREOct 9, 2026 · close 167.32

Daily candles, adjusted for splits and dividends. Green arrows are insider buys, red are sells, sized by value. Click a marked bar to open the signal.Charts by TradingView Lightweight Charts™

Signals

This insider’s open-market buys and sells, scored.

ScoreCompanyValueHoldingsPrice contextFiled
40Moderate
GWREsell 510b5-1
Guidewire Software, Inc.
$1.9M
13,195 shares
-23%-
41Moderate
GWREsell 5
Guidewire Software, Inc.
$164k
1,001 shares
-3%+33% from low-38% from high
30Weak
GWREsell 510b5-1
Guidewire Software, Inc.
$643k
3,317 shares
-9%+16% from low-26% from high
22Weak
GWREsell 310b5-1
Guidewire Software, Inc.
$178k
798 shares
-2%+30% from low-17% from high
22Weak
GWREsell 310b5-1
Guidewire Software, Inc.
$196k
798 shares
-2%+52% from low-3% from high
40Moderate
GWREsell 610b5-1
Guidewire Software, Inc.
$1.8M
7,162 shares
-16%+48% from low-6% from high
45Moderate
GWREsell 5
Guidewire Software, Inc.
$1.7M
7,149 shares
-14%+48% from low-6% from high
14Weak
GWREsell 210b5-1
Guidewire Software, Inc.
$169k
799 shares
-2%+29% from low-16% from high
29Weak
GWREsell 410b5-1
Guidewire Software, Inc.
$548k
2,482 shares
-6%+33% from low-14% from high
24Weak
GWREsell 610b5-1
Guidewire Software, Inc.
$306k
1,230 shares
-3%+49% from low-4% from high
33Weak
GWREsell 610b5-1
Guidewire Software, Inc.
$868k
4,511 shares
-10%+15% from low-12% from high
16Weak
GWREsell 510b5-1
Guidewire Software, Inc.
$47k
270 shares
-1%-
26Weak
GWREsell 410b5-1
Guidewire Software, Inc.
$397k
2,303 shares
-5%-

Planned sales

Form 144 notices this insider filed before selling restricted or control stock, newest first.

FiledCompanySharesValueSale datePast 3 months
Oct 9, 2026 GWRE
GUIDEWIRE SOFTWARE, INC.
9,187
0.01% of outstanding
$1.5MOct 9, 2026$1.9M
Sep 18, 2025 GWRE
GUIDEWIRE SOFTWARE, INC.
7,162
0.01% of outstanding
$1.8MSep 18, 2025$2.5M
Sep 16, 2025 GWRE
Guidewire Software, Inc,
7,149
0.01% of outstanding
$1.7MSep 16, 2025$1.0M
Aug 18, 2025 GWRE
GUIDEWIRE SOFTWARE, INC.
799
0.00% of outstanding
$169kAug 18, 2025$854k
Jul 14, 2025 GWRE
GUIDEWIRE SOFTWARE, INC.
2,482
0.00% of outstanding
$548kJul 14, 2025$306k
Jun 17, 2025 GWRE
Guidewire Software, Inc.
1,230
0.00% of outstanding
$306kJun 17, 2025$868k
Mar 19, 2025 GWRE
GUIDEWIRE SOFTWARE, INC.
3,460
0.00% of outstanding
$669kMar 19, 2025$246k
Mar 18, 2025 GWRE
Guidewire Software, Inc.
1,051
0.00% of outstanding
$199kMar 18, 2025$444k
Jan 15, 2025 GWRE
GUIDEWIRE SOFTWARE, INC.
270
0.00% of outstanding
$47kJan 15, 2025$397k
Dec 19, 2024 GWRE
GUIDEWIRE SOFTWARE, INC.
794
0.00% of outstanding
$138kDec 19, 2024$258k
Dec 18, 2024 GWRE
Guidewire Software, Inc.
1,509
0.00% of outstanding
$258kDec 17, 2024$1.8M

Transactions

Every row this insider has filed, 30 in all, newest first.

DateCompanyTransactionSharesPriceValueHoldings afterFiled
Sep 17, 2026GWRE
Guidewire Software, Inc.
SOpen-market sale
Common Stock10b5-1
-11,814$144.47$1.7M45,93922 d ago
Sep 18, 2026GWRE
Guidewire Software, Inc.
SOpen-market sale
Common Stock10b5-1
-1,381$144.98$200k44,55822 d ago
Sep 15, 2026GWRE
Guidewire Software, Inc.
MOption exercise
Common Stock
+19,701$0.00$057,75328 d ago
Sep 15, 2026GWRE
Guidewire Software, Inc.
MOption exercise
Performance Sharesderivative
-19,701$0.00$0028 d ago
Sep 11, 2026GWRE
Guidewire Software, Inc.
AGrant or award
Common Stock
+8,034$0.00$038,05229 d ago
Sep 11, 2026GWRE
Guidewire Software, Inc.
AGrant or award
Performance Sharesderivative
+8,034$0.00$08,03429 d ago
Mar 17, 2026GWRE
Guidewire Software, Inc.
SOpen-market sale
Common Stock
-1,001$163.86$164k32,701Mar 18, 2026
Dec 16, 2025GWRE
Guidewire Software, Inc.
SOpen-market sale
Common Stock10b5-1
-1,457$192.08$280k35,562Dec 18, 2025
Dec 18, 2025GWRE
Guidewire Software, Inc.
SOpen-market sale
Common Stock10b5-1
-1,860$195.00$363k33,702Dec 18, 2025
Nov 17, 2025GWRE
Guidewire Software, Inc.
SOpen-market sale
Common Stock10b5-1
-798$222.54$178k37,019Nov 17, 2025
Oct 20, 2025GWRE
Guidewire Software, Inc.
SOpen-market sale
Common Stock10b5-1
-798$245.70$196k37,817Oct 21, 2025
Sep 18, 2025GWRE
Guidewire Software, Inc.
SOpen-market sale
Common Stock10b5-1
-1,878$247.21$464k43,899Sep 22, 2025
Sep 18, 2025GWRE
Guidewire Software, Inc.
SOpen-market sale
Common Stock10b5-1
-1,197$248.16$297k42,702Sep 22, 2025
Sep 18, 2025GWRE
Guidewire Software, Inc.
SOpen-market sale
Common Stock10b5-1
-1,940$249.35$484k40,762Sep 22, 2025
Sep 18, 2025GWRE
Guidewire Software, Inc.
SOpen-market sale
Common Stock10b5-1
-2,147$250.12$537k38,615Sep 22, 2025
Sep 15, 2025GWRE
Guidewire Software, Inc.
MOption exercise
Common Stock
+10,597$0.00$052,926Sep 17, 2025
Sep 16, 2025GWRE
Guidewire Software, Inc.
SOpen-market sale
Common Stock
-7,149$242.87$1.7M45,777Sep 17, 2025
Sep 15, 2025GWRE
Guidewire Software, Inc.
MOption exercise
Performance Sharesderivative
-10,597$0.00$00Sep 17, 2025
Sep 11, 2025GWRE
Guidewire Software, Inc.
AGrant or award
Common Stock
+5,687$0.00$042,329Sep 15, 2025
Sep 11, 2025GWRE
Guidewire Software, Inc.
AGrant or award
Performance Sharesderivative
+5,687$0.00$05,687Sep 15, 2025
Aug 18, 2025GWRE
Guidewire Software, Inc.
SOpen-market sale
Common Stock10b5-1
-799$211.61$169k36,642Aug 18, 2025
Jul 14, 2025GWRE
Guidewire Software, Inc.
SOpen-market sale
Common Stock10b5-1
-2,482$220.65$548k37,441Jul 15, 2025
Jun 17, 2025GWRE
Guidewire Software, Inc.
SOpen-market sale
Common Stock10b5-1
-1,230$248.94$306k39,923Jun 18, 2025
Mar 18, 2025GWRE
Guidewire Software, Inc.
SOpen-market sale
Common Stock10b5-1
-1,051$189.41$199k44,613Mar 19, 2025
Mar 19, 2025GWRE
Guidewire Software, Inc.
SOpen-market sale
Common Stock10b5-1
-841$191.30$161k43,772Mar 19, 2025
Mar 19, 2025GWRE
Guidewire Software, Inc.
SOpen-market sale
Common Stock10b5-1
-1,827$193.51$354k41,945Mar 19, 2025
Mar 19, 2025GWRE
Guidewire Software, Inc.
SOpen-market sale
Common Stock10b5-1
-792$194.61$154k41,153Mar 19, 2025
Jan 15, 2025GWRE
Guidewire Software, Inc.
SOpen-market sale
Common Stock10b5-1
-270$174.78$47k45,664Jan 15, 2025
Dec 17, 2024GWRE
Guidewire Software, Inc.
SOpen-market sale
Common Stock10b5-1
-1,509$171.06$258k46,728Dec 19, 2024
Dec 19, 2024GWRE
Guidewire Software, Inc.
SOpen-market sale
Common Stock10b5-1
-794$174.43$138k45,934Dec 19, 2024

Questions about James Winston King

Answered from the filings on this page, as of the latest one.

Is James Winston King buying or selling?

In the last 12 months James Winston King reported 0 open-market buys worth $0 and 5 open-market sells worth $3.1M on SEC Form 4; the latest was sold $1.9M of GWRE on Sep 17, 2026. Grants, option exercises and tax withholding are not counted.

How did James Winston King's past buys perform?

Not measured yet. InsiderTell needs three past buys with six months of prices to publish a track record, and James Winston King has 0.

Where does James Winston King file Form 4?

James Winston King has filed Form 4 at GWRE (Guidewire Software, Inc.) as Chief Admin Officer, Gen Couns. A Form 4 is required of officers, directors and holders of more than 10% of a share class within two business days of a trade.

Not investment advice. Scores and forward returns are decision support built from public SEC filings and past prices; they describe what happened after comparable filings, not what will happen after this one. Do your own research and size your risk.

James Winston King: insider trades and track record | InsiderTell