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GWREGuidewire Software, Inc. · Insider ownership research

Guidewire Software, Inc. insiders sold $48.3M in the past 12 months. How much of their stake is that?

Insiders sold $48.3M in the past 12 months.76% was sold under disclosed trading plans, 24% to cover taxes. The largest seller, Michael Rosenbaum (Chief Executive Officer, Director), sold $23.3M.Share-of-stake figures for this company are being verified and will be added when that check is finished. Why

Updated Oct 13, 2026 from SEC filings · covers Oct 14, 2025 to Oct 13, 2026
$23.3M
largest seller, Michael Rosenbaum, past 12 months
76%
of sales were under disclosed trading plans, past 12 months
5 of 13
officers and directors sold shares, past 12 months
Is this normal? More than usual: about 2x the 5-year average. 5 insiders sold; the average is 6 a year. Year by year
Latest filing: Filed Oct 5 for a sale on Oct 5. Michael Rosenbaum sold 1.2K shares ($183K) under a disclosed plan. Filing
SEC ownership filings: 97 filed in the 12 months to Oct 13, 2026; 1,551 on record since Jan 24, 2012 · See the evidence

What stands out

Selling picked up in the last 90 days: officers and directors sold 195K shares, against an average of 37K per 90 days earlier in the period. Most of it was Michael Rosenbaum (87K shares in the last 90 days) and John Mullen (58K shares in the last 90 days); 80% of these sales were under disclosed plans.Michael Rosenbaum: largest recent sale, Sep 17, 2026 · John Mullen: largest recent sale, Sep 17, 2026

A share of stake is shown for 0 of the 5 officers and directors who sold. 13 are left out

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Left out: Michael Rosenbaum, John Mullen, Jeffrey Cooper, James King, Catherine Lego, Margaret Dillon, David Peterson, Rajani Ramanathan, Michael Keller, David Bauer, Mark Anquillare, Jeffrey Sloan and Karl Vollert (share of stake is being verified).
Disclosed company stock is not an insider's whole wealth.

Who sold, and how much of their stake

Officers and directors, past 12 months. Their share of stake is being verified and is not shown yet; amounts and trading plans are below.

Michael Rosenbaum
Chief Executive Officer, Director
Not confirmed
Share of stake not shown: share of stake is being verified. Why
$23.3M92% planned, 8% to cover taxes
John Mullen
President
Not confirmed
Share of stake not shown: share of stake is being verified. Why
$13.5M35% planned, 65% to cover taxes
Jeffrey Cooper
Chief Financial Officer
Not confirmed
Share of stake not shown: share of stake is being verified. Why
$7.1M91% planned, 9% to cover taxes
James King
Chief Admin Officer, Gen Couns
Not confirmed
Share of stake not shown: share of stake is being verified. Why
$3.4M92% planned, 8% to cover taxes
David Peterson
Chief Accounting Officer
Not confirmed
Share of stake not shown: share of stake is being verified. Why
$918K88% planned, 12% to cover taxes
Amounts, filings and trading plans for each seller

Selling by month

Officers and directors, Oct 2025 to Oct 2026. Each sale is counted once: under a disclosed plan, else to cover taxes, else no plan disclosed.

Disclosed planTo cover taxesOne dollar scale for every month; the tallest bar is labeled
Oct 2025: $898K under a disclosed planOctNov 2025: $2.1M under a disclosed planNovDec 2025: $3.5M under a disclosed planDec 2025: $2.8M to cover taxesDecJan 2026: $636K under a disclosed planJanFeb 2026: $624K under a disclosed planFebMar 2026: $1.7M under a disclosed planMar 2026: $2.4M to cover taxesMarApr 2026: $657K under a disclosed planAprMay 2026: $654K under a disclosed planMayJun 2026: $1.6M under a disclosed planJun 2026: $936K to cover taxesJunJul 2026: $892K under a disclosed planJulAug 2026: $4.9M under a disclosed planAugSep 2026: $18.1M under a disclosed planSep 2026: $5.7M to cover taxes$23.8MSepOct 2026: $183K under a disclosed planOct

Recent activity

Past 30 days, Sep 14, 2026 to Oct 13, 2026
Oct 5, 2026Michael Rosenbaum sold 1.2K shares ($183K) under a disclosed trading plan.
WhoSharesPrice% of total stakeTotal stake afterTrade dateFiled
Michael Rosenbaum
Chief Executive Officer, Director
1,200$152.52n/an/aOct 5, 2026Oct 5, 2026
Sep 28, 2026Michael Rosenbaum sold 1.2K shares ($171K) under a disclosed trading plan.
WhoSharesPrice% of total stakeTotal stake afterTrade dateFiled
Michael Rosenbaum
Chief Executive Officer, Director
1,200$142.65n/an/aSep 28, 2026Sep 30, 2026
Sep 21, 2026Michael Rosenbaum sold 1.2K shares ($175K) under a disclosed trading plan.
WhoSharesPrice% of total stakeTotal stake afterTrade dateFiled
Michael Rosenbaum
Chief Executive Officer, Director
1,200$145.92n/an/aSep 21, 2026Sep 21, 2026
Sep 18, 20262 executives sold 11K shares ($1.6M) under a disclosed trading plan.
WhoSharesPrice% of total stakeTotal stake afterTrade dateFiled
Jeffrey Cooper
Chief Financial Officer
9,941$142.61n/an/aSep 18, 2026Sep 21, 2026
James King
Chief Admin Officer, Gen Couns
1,381$144.98n/an/aSep 18, 2026Sep 21, 2026
Sep 17, 20265 executives sold 149K shares ($21.5M) to cover taxes on vesting stock.
WhoSharesPrice% of total stakeTotal stake afterTrade dateFiled
Michael Rosenbaum
Chief Executive Officer, Director
Also under a disclosed plan
72,290$144.47n/an/aSep 17, 2026Sep 21, 2026
John Mullen
President
39,683$144.47n/an/aSep 17, 2026Sep 21, 2026
Jeffrey Cooper
Chief Financial Officer
Also under a disclosed plan
23,234$144.47n/an/aSep 17, 2026Sep 21, 2026
James King
Chief Admin Officer, Gen Couns
Also under a disclosed plan
11,814$144.47n/an/aSep 17, 2026Sep 21, 2026
David Peterson
Chief Accounting Officer
Also under a disclosed plan
1,905$144.47n/an/aSep 17, 2026Sep 21, 2026
Show all 6 events
Sep 14, 2026Michael Rosenbaum sold 1.2K shares ($175K) under a disclosed trading plan.
WhoSharesPrice% of total stakeTotal stake afterTrade dateFiled
Michael Rosenbaum
Chief Executive Officer, Director
1,200$145.87n/an/aSep 14, 2026Sep 14, 2026

"% of total stake" is the shares in an event against all the vested shares the person held that day, across every share class and holding entity, after that day's vesting. "n/a" means the person's holdings are not confirmed, or the row is a purchase. "Holdings record incomplete" means more shares were sold than the filings show the person held that day, so a percentage would be wrong.

Common questions

Is the Guidewire Software, Inc. CEO selling stock?

Yes. Michael Rosenbaum sold 151K shares ($23.3M) in the past 12 months, 92% of it under a trading plan disclosed in the filings.

Why are Guidewire Software, Inc. insiders selling?

Filings rarely give a reason, and we don't guess at one. What they show is how the sales were made: 76% of sales by value ran under 10b5-1 trading plans disclosed in the filings and 24% were to cover taxes. A trading plan schedules sales in advance.

Are any Guidewire Software, Inc. insiders buying?

No. Officers and directors reported no purchases in the past 12 months.

The evidence

Who sold5 officers and directors: amount, % of holdings, trading plan
Who soldAmount% of holdingsTrading plan
Michael Rosenbaum
Chief Executive Officer, Director
$23.3M
151K shares
Not confirmed
share of stake is being verified. Why
92% under a disclosed plan, 8% to cover taxes
John Mullen
President
$13.5M
83K shares
Not confirmed
share of stake is being verified. Why
35% under a disclosed plan, 65% to cover taxes
Jeffrey Cooper
Chief Financial Officer
$7.1M
48K shares
Not confirmed
share of stake is being verified. Why
91% under a disclosed plan, 9% to cover taxes
James King
Chief Admin Officer, Gen Couns
$3.4M
22K shares
Not confirmed
share of stake is being verified. Why
92% under a disclosed plan, 8% to cover taxes
David Peterson
Chief Accounting Officer
$918K
5.3K shares
Not confirmed
share of stake is being verified. Why
88% under a disclosed plan, 12% to cover taxes
The full ownership picture0 of 13 officers and directors confirmed

Vested shares across all share classes, held directly and through trusts, LLCs and family members, as reported on SEC Forms 3, 4 and 5. Unvested awards and options are never counted as owned shares.

InsiderHeld Oct 13, 2025SoldHeld Oct 13, 2026Still held
Michael Rosenbaum
!
Holdings and share of stake are being verified. Share-of-stake figures and holdings for this company are held back while they are verified. Sales and other transactions for Michael Rosenbaum are complete.
Chief Executive Officer, Director
n/a−151Kn/an/a
Vesting, gifts, unvested awards and holding lines for Michael Rosenbaum

Holdings and share of stake are being verified. Sales, proceeds, plan and tax status and dates for Michael Rosenbaum are complete; balances and unit counts will be added when the check is finished.

0gifted (net of own trusts)
John Mullen
!
Holdings and share of stake are being verified. Share-of-stake figures and holdings for this company are held back while they are verified. Sales and other transactions for John Mullen are complete.
President
n/a−83Kn/an/a
Vesting, gifts, unvested awards and holding lines for John Mullen

Holdings and share of stake are being verified. Sales, proceeds, plan and tax status and dates for John Mullen are complete; balances and unit counts will be added when the check is finished.

0gifted (net of own trusts)
Jeffrey Cooper
!
Holdings and share of stake are being verified. Share-of-stake figures and holdings for this company are held back while they are verified. Sales and other transactions for Jeffrey Cooper are complete.
Chief Financial Officer
n/a−48Kn/an/a
Vesting, gifts, unvested awards and holding lines for Jeffrey Cooper

Holdings and share of stake are being verified. Sales, proceeds, plan and tax status and dates for Jeffrey Cooper are complete; balances and unit counts will be added when the check is finished.

0gifted (net of own trusts)
James King
!
Holdings and share of stake are being verified. Share-of-stake figures and holdings for this company are held back while they are verified. Sales and other transactions for James King are complete.
Chief Admin Officer, Gen Couns
n/a−22Kn/an/a
Vesting, gifts, unvested awards and holding lines for James King

Holdings and share of stake are being verified. Sales, proceeds, plan and tax status and dates for James King are complete; balances and unit counts will be added when the check is finished.

0gifted (net of own trusts)
Catherine Lego
!
Holdings and share of stake are being verified. Share-of-stake figures and holdings for this company are held back while they are verified. Sales and other transactions for Catherine Lego are complete.
Director
n/a0n/an/a
Vesting, gifts, unvested awards and holding lines for Catherine Lego

Holdings and share of stake are being verified. Sales, proceeds, plan and tax status and dates for Catherine Lego are complete; balances and unit counts will be added when the check is finished.

0gifted (net of own trusts)
Margaret Dillon
!
Holdings and share of stake are being verified. Share-of-stake figures and holdings for this company are held back while they are verified. Sales and other transactions for Margaret Dillon are complete.
Director
n/a0n/an/a
Vesting, gifts, unvested awards and holding lines for Margaret Dillon

Holdings and share of stake are being verified. Sales, proceeds, plan and tax status and dates for Margaret Dillon are complete; balances and unit counts will be added when the check is finished.

0gifted (net of own trusts)
David Peterson
!
Holdings and share of stake are being verified. Share-of-stake figures and holdings for this company are held back while they are verified. Sales and other transactions for David Peterson are complete.
Chief Accounting Officer
n/a−5.3Kn/an/a
Vesting, gifts, unvested awards and holding lines for David Peterson

Holdings and share of stake are being verified. Sales, proceeds, plan and tax status and dates for David Peterson are complete; balances and unit counts will be added when the check is finished.

0gifted (net of own trusts)
Rajani Ramanathan
!
Holdings and share of stake are being verified. Share-of-stake figures and holdings for this company are held back while they are verified. Sales and other transactions for Rajani Ramanathan are complete.
Director
n/a0n/an/a
Vesting, gifts, unvested awards and holding lines for Rajani Ramanathan

Holdings and share of stake are being verified. Sales, proceeds, plan and tax status and dates for Rajani Ramanathan are complete; balances and unit counts will be added when the check is finished.

0gifted (net of own trusts)
Michael Keller
!
Holdings and share of stake are being verified. Share-of-stake figures and holdings for this company are held back while they are verified. Sales and other transactions for Michael Keller are complete.
Director
n/a0n/an/a
Vesting, gifts, unvested awards and holding lines for Michael Keller

Holdings and share of stake are being verified. Sales, proceeds, plan and tax status and dates for Michael Keller are complete; balances and unit counts will be added when the check is finished.

0gifted (net of own trusts)
David Bauer
!
Holdings and share of stake are being verified. Share-of-stake figures and holdings for this company are held back while they are verified. Sales and other transactions for David Bauer are complete.
Director
n/a0n/an/a
Vesting, gifts, unvested awards and holding lines for David Bauer

Holdings and share of stake are being verified. Sales, proceeds, plan and tax status and dates for David Bauer are complete; balances and unit counts will be added when the check is finished.

0gifted (net of own trusts)
Mark Anquillare
!
Holdings and share of stake are being verified. Share-of-stake figures and holdings for this company are held back while they are verified. Sales and other transactions for Mark Anquillare are complete.
Director
n/a0n/an/a
Vesting, gifts, unvested awards and holding lines for Mark Anquillare

Holdings and share of stake are being verified. Sales, proceeds, plan and tax status and dates for Mark Anquillare are complete; balances and unit counts will be added when the check is finished.

0gifted (net of own trusts)
Jeffrey Sloan
!
Holdings and share of stake are being verified. Share-of-stake figures and holdings for this company are held back while they are verified. Sales and other transactions for Jeffrey Sloan are complete.
Director
n/a0n/an/a
Vesting, gifts, unvested awards and holding lines for Jeffrey Sloan

Holdings and share of stake are being verified. Sales, proceeds, plan and tax status and dates for Jeffrey Sloan are complete; balances and unit counts will be added when the check is finished.

0gifted (net of own trusts)
Karl Vollert
!
Holdings and share of stake are being verified. Share-of-stake figures and holdings for this company are held back while they are verified. Sales and other transactions for Karl Vollert are complete.
Director
n/a0n/an/a
Vesting, gifts, unvested awards and holding lines for Karl Vollert

Holdings and share of stake are being verified. Sales, proceeds, plan and tax status and dates for Karl Vollert are complete; balances and unit counts will be added when the check is finished.

0gifted (net of own trusts)

Holdings and share of stake for Guidewire Software, Inc. are being verified, so no balances, unit counts or percentages are shown. Sales, proceeds, plan and tax status, titles and dates come straight from individual filings.

What explains the selling$48.3M of sales by plan status, purpose, seller and month

Officer and director open-market sales: $48.3M across 308,801 shares. Plan status and stated purpose are separate questions, and a sale can have both.

By plan status

The lighter segment is sales with no plan disclosed in the filing ($11.8M), including tax-related sales outside a plan.

Taxes

$29.1M of sales (60.3%) cite tax obligations in their footnotes, $17.3M of them also under a plan. Example: David Peterson, Sep 17, 2026

SellerShares soldProceedsUnder a disclosed planShare of totalSales dates
Michael Rosenbaum
Chief Executive Officer, Director
151K$23.3M92%48%Oct 20, 2025 to Oct 5, 2026
John Mullen
President
83K$13.5M35%28%Nov 3, 2025 to Sep 17, 2026
Jeffrey Cooper
Chief Financial Officer
48K$7.1M91%15%Dec 16, 2025 to Sep 18, 2026
James King
Chief Admin Officer, Gen Couns
22K$3.4M92%7%Oct 20, 2025 to Sep 18, 2026
David Peterson
Chief Accounting Officer
5.3K$918K88%2%Dec 16, 2025 to Sep 17, 2026

Sales by month

MonthSale proceedsDisclosed planTo cover taxesNo plan disclosed
Oct 2025$898K$898K$0$0
Nov 2025$2.1M$2.1M$0$0
Dec 2025$6.3M$3.5M$2.8M$0
Jan 2026$636K$636K$0$0
Feb 2026$624K$624K$0$0
Mar 2026$4.1M$1.7M$2.4M$0
Apr 2026$657K$657K$0$0
May 2026$654K$654K$0$0
Jun 2026$2.6M$1.6M$936K$0
Jul 2026$892K$892K$0$0
Aug 2026$4.9M$4.9M$0$0
Sep 2026$23.8M$18.1M$5.7M$0
Oct 2026$183K$183K$0$0
Is this normal? Selling year by year5 earlier years to compare with

More than usual: about 2x the 5-year average. 5 insiders sold; the average is 6 a year.

12 months endingShares soldInsiders who soldProceeds
Oct 13, 2026
Latest 12 months
309K5$48.3M
Oct 13, 2025
1 year earlier
245K7$54.1M
Oct 13, 2024
2 years earlier
124K5$17.6M
Oct 14, 2023
3 years earlier
153K5$12.4M
Oct 14, 2022
4 years earlier
93K6$7.2M
Oct 14, 2021
5 years earlier
153K8$17.6M

Open-market sales (Form 4 code S) by people who were officers or directors, in split-adjusted shares. Earlier years include people who have since left. A sale that an outside holder also reports (a family trust, a fund) is counted with outside holders in every year. Shares, not dollars, are compared, so a change in the stock price doesn't look like a change in selling. Years the filings don't fully cover are shown but left out of the average.

Known gaps and uncertainty13 officers and directors not confirmed

Holdings and share of stake are being verified. Balances, unit counts and every share-of-stake figure for Guidewire Software, Inc. are held back until that check is finished. Sales, proceeds, plan and tax status, titles and dates come straight from individual filings and are complete.

External context: we only cite outside events when a documented connection exists. None is shown for this period.

Sources and methodology1,551 filings on record, 97 filed in the 12-month period, and how we read them

All 1,551 Forms 3, 4 and 5 on record for Guidewire Software, Inc. (SEC CIK 1528396), filed from Jan 24, 2012 to Oct 5, 2026; 97 of them were filed in the 12 months this page covers, retrieved from SEC EDGAR on Oct 13, 2026. Prices are the ones reported in each filing, often weighted averages.

Holdings. Each holding line (a share class plus an owner, such as a trust or LLC) carries its last reported balance forward. Entities first reported during the period start at zero, so transfers between an insider's own trusts don't count as selling. Lines not reported for three years or more are listed separately and left out of totals.

Sales. A sale counts as under a 10b5-1 plan if its footnote cites one or the filing's Rule 10b5-1 box is checked, and as tax-related if its footnote cites tax obligations or sell-to-cover. Shares withheld by the company for taxes are listed separately. Sales with neither attribute are labeled "no plan disclosed".

Full methodology

Former or inactive filers (28)No filing in 18 months; last reported balances, not in any total
NameLast filedLast reported balance
Paul LavinDec 23, 202413,796 shares, last reported balance as of Dec 22, 2024
Priscilla HungDec 20, 202338,131 shares, last reported balance as of Dec 20, 2023
Marcus RyuDec 19, 202310,555 shares, last reported balance as of Dec 19, 2023
Andrew BrownJun 23, 20228,524 shares, last reported balance as of Jun 23, 2022
Michael PolelleMar 18, 20227,241 shares, last reported balance as of Mar 18, 2022
Frank ODowd Jr.Sep 21, 202128,275 shares, last reported balance as of Sep 17, 2021
Steven SherryJun 22, 2020No balance on record
Curtis SmithDec 19, 20194,493 shares, last reported balance as of Dec 18, 2019
Guy DuboisDec 10, 201910,970 shares, last reported balance as of Dec 6, 2019
Clifton WeatherfordSep 20, 201914,341 shares, last reported balance as of Sep 19, 2019
Craig ConwayDec 17, 201811,103 shares, last reported balance as of Dec 17, 2018
Peter GassnerDec 10, 201813,723 shares, last reported balance as of Dec 6, 2018
Ali KheirolomoomJun 20, 20185,225 shares, last reported balance as of Jun 20, 2018
Richard HartMar 6, 20183,662 shares, last reported balance as of Mar 5, 2018
Scott RozaOct 16, 20171,300 shares, last reported balance as of Oct 16, 2017
John CavooresDec 4, 201520,659 shares, last reported balance as of Dec 3, 2015
Karen BlasingMar 9, 2015No balance on record
Jeremy HenricksonJul 16, 201421,976 shares, last reported balance as of Jul 14, 2014
Alexander NaddaffJun 5, 20142,422 shares, last reported balance as of Jun 3, 2014
Kenneth BransonMar 6, 2014856,979 shares, last reported balance as of Mar 4, 2014
Craig RamseyDec 9, 2013338,271 shares, last reported balance as of Dec 5, 2013
Neal DempseySep 9, 201380,631 shares, last reported balance as of Sep 6, 2013
Neal DempseySep 9, 2013279,666 shares, last reported balance as of Jan 24, 2012
Steven KrauszJun 20, 201312,797 shares, last reported balance as of Jun 20, 2013
Steven KrauszJun 20, 2013No balance on record
John TrueMar 19, 201324,457 shares, last reported balance as of Mar 15, 2013
BAY PARTNERS X LPDec 3, 20125,122,087 shares, last reported balance as of Nov 29, 2012
PRESIDIO MANAGEMENT GROUP VIII L L CSep 25, 20125,109,872 shares, last reported balance as of Sep 25, 2012

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