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BENTLEY SYSTEMS INC

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438
SEC CIK
0001031308
Parsed reports
660

Last 12 months

Inside the activity.

0 purchase rows · 2 sale rows

Disclosed non-derivative P/S rows, by transaction month. Includes amendments and private transactions.
Monthly counts
MonthPurchasesSales
Nov 202501
Dec 202500
Jan 202600
Feb 202600
Mar 202601
Apr 202600
May 202600
Jun 202600
Jul 202600
Aug 202600
Sep 202600
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Purchases/sales include open-market and private transactions. Plan disclosure applies to the filing; individual rows may differ. “Not disclosed” is not “unplanned.”

The cutoff filters transaction history only. Company summaries and owner relationships show the latest available disclosures. Parser corrections can improve historical records.

Transaction dateOwner / reported roleActivity / securityShares / unitsReported priceReported valueDetails
December 15, 2025 Filed Dec 17, 2025 21:15 UTC
Cumins NicholasDirector · Chief Executive Officer
Tax withholdingClass B Common Stock 17,162 $40.25 $690,770.50
Disclosure

SEC source: 0001104659-25-122055 · tm2532204-17_4seq1.xml · nonDerivative · entry 1

Cumins Nicholas · CIK 0001896877 · Director · Chief Executive Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 423,112

F1 · kind: Represents shares withheld by the Issuer to cover taxes due by the Reporting Person upon the vesting of awards previously granted to the Reporting Person.

Read SEC document
December 15, 2025 Filed Dec 17, 2025 21:15 UTC
Lee James KChief Operating Officer
Tax withholdingClass B Common Stock 9,166 $40.25 $368,931.50
Disclosure

SEC source: 0001104659-25-122054 · tm2532204-16_4seq1.xml · nonDerivative · entry 1

Lee James K · CIK 0002052647 · Chief Operating Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 163,290

F1 · kind: Represents shares withheld by the Issuer to cover taxes due by the Reporting Person upon the vesting of awards previously granted to the Reporting Person.

Read SEC document
December 15, 2025 Filed Dec 17, 2025 21:15 UTC
Shaman David R.Chief Legal Officer
GiftClass B Common Stock 2,500 $0.00 $0.00
Disclosure

SEC source: 0001104659-25-122051 · tm2532204-15_4seq1.xml · nonDerivative · entry 3

Shaman David R. · CIK 0001825193 · Chief Legal Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 632,755

Read SEC document
December 15, 2025 Filed Dec 17, 2025 21:15 UTC
Shaman David R.Chief Legal Officer
Tax withholdingClass B Common Stock 730 $40.25 $29,382.50
Disclosure

SEC source: 0001104659-25-122051 · tm2532204-15_4seq1.xml · nonDerivative · entry 2

Shaman David R. · CIK 0001825193 · Chief Legal Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 635,255

F2 · kind: Reflects shares withheld from restricted stock unit awards to cover tax obligations for colleagues eligible for retirement vesting under the terms of the Company's 2020 Omnibus Incentive Plan.

Read SEC document
December 15, 2025 Filed Dec 17, 2025 21:15 UTC
Shaman David R.Chief Legal Officer
Tax withholdingClass B Common Stock 4,165 $40.25 $167,641.25
Disclosure

SEC source: 0001104659-25-122051 · tm2532204-15_4seq1.xml · nonDerivative · entry 1

Shaman David R. · CIK 0001825193 · Chief Legal Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 635,985

F1 · kind: Represents shares withheld by the Issuer to cover taxes due by the Reporting Person upon the vesting of awards previously granted to the Reporting Person.

Read SEC document
December 11, 2025 Filed Dec 15, 2025 21:26 UTC
Andre WernerChief Financial Officer
GrantClass B Common Stock 157 $0.00 $0.00
Disclosure

SEC source: 0001104659-25-121171 · tm2532204-14_4seq1.xml · nonDerivative · entry 1

Andre Werner · CIK 0001825257 · Chief Financial Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 351,363

F1 · kind: Represents dividend equivalent rights that accrued to the Reporting Person in connection with a dividend paid by the Issuer on awards previously granted and vest on the same terms as the awards to which they relate.

Read SEC document
December 11, 2025 Filed Dec 15, 2025 21:25 UTC
Trimback Thomas FChief Accounting Officer
GrantClass B Common Stock 16 $0.00 $0.00
Disclosure

SEC source: 0001104659-25-121167 · tm2532204-13_4seq1.xml · nonDerivative · entry 1

Trimback Thomas F · CIK 0002015992 · Chief Accounting Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 13,822

F1 · kind: Represents dividend equivalent rights that accrued to the Reporting Person in connection with a dividend paid by the Issuer on awards previously granted and vest on the same terms as the awards to which they relate.

Read SEC document
December 11, 2025 Filed Dec 15, 2025 21:24 UTC
Bentley Raymond B.Director · 10% owner
GrantClass B Common Stock 1,730 $0.00 $0.00
Disclosure

SEC source: 0001104659-25-121164 · tm2532204-12_4seq1.xml · nonDerivative · entry 1

Bentley Raymond B. · CIK 0001825229 · Director · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 15,103,583

F1 · kind: Represents dividend equivalent rights that accrued to the Reporting Person in connection with a dividend paid by the Issuer on awards previously granted and vest on the same terms as the awards to which they relate.

Read SEC document
December 11, 2025 Filed Dec 15, 2025 21:23 UTC
Bentley Keith A.Director · 10% owner
GrantClass B Common Stock 1,284 $0.00 $0.00
Disclosure

SEC source: 0001104659-25-121161 · tm2532204-11_4seq1.xml · nonDerivative · entry 1

Bentley Keith A. · CIK 0001825187 · Director · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 3,961,635

F1 · kind: Represents dividend equivalent rights that accrued to the Reporting Person in connection with a dividend paid by the Issuer on awards previously granted and vest on the same terms as the awards to which they relate.

Read SEC document
December 11, 2025 Filed Dec 15, 2025 21:21 UTC
Cumins NicholasDirector · Chief Executive Officer
GrantClass B Common Stock 485 $0.00 $0.00
Disclosure

SEC source: 0001104659-25-121159 · tm2532204-10_4seq1.xml · nonDerivative · entry 1

Cumins Nicholas · CIK 0001896877 · Director · Chief Executive Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 440,274

F1 · kind: Represents dividend equivalent rights that accrued to the Reporting Person in connection with a dividend paid by the Issuer on awards previously granted and vest on the same terms as the awards to which they relate.

Read SEC document
December 11, 2025 Filed Dec 15, 2025 21:19 UTC
Moutte JulienChief Technology Officer
GrantClass B Common Stock 72 $0.00 $0.00
Disclosure

SEC source: 0001104659-25-121155 · tm2532204-8_4seq1.xml · nonDerivative · entry 1

Moutte Julien · CIK 0002062214 · Chief Technology Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 68,975

F1 · kind: Represents dividend equivalent rights that accrued to the Reporting Person in connection with a dividend paid by the Issuer on awards previously granted and vest on the same terms as the awards to which they relate.

Read SEC document
December 11, 2025 Filed Dec 15, 2025 21:20 UTC GrantClass B Common Stock 85 $0.00 $0.00
Disclosure

SEC source: 0001104659-25-121156 · tm2532204-9_4seq1.xml · nonDerivative · entry 1

Griswold Kirk B. · CIK 0001825243 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 461,212

F1 · kind: Represents dividend equivalent rights that accrued to the Reporting Person in connection with a dividend paid by the Issuer on awards previously granted and vest on the same terms as the awards to which they relate.

Read SEC document
December 11, 2025 Filed Dec 15, 2025 21:18 UTC
Bentley Barry J.Director · 10% owner
GrantClass B Common Stock 5 $0.00 $0.00
Disclosure

SEC source: 0001104659-25-121154 · tm2532204-7_4seq1.xml · nonDerivative · entry 1

Bentley Barry J. · CIK 0001825188 · Director · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 11,838,258

F1 · kind: Represents dividend equivalent rights that accrued to the Reporting Person in connection with a dividend paid by the Issuer on awards previously granted and vest on the same terms as the awards to which they relate.

Read SEC document
December 11, 2025 Filed Dec 15, 2025 21:18 UTC
Lee James KChief Operating Officer
GrantClass B Common Stock 264 $0.00 $0.00
Disclosure

SEC source: 0001104659-25-121152 · tm2532204-6_4seq1.xml · nonDerivative · entry 1

Lee James K · CIK 0002052647 · Chief Operating Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 172,456

F1 · kind: Represents dividend equivalent rights that accrued to the Reporting Person in connection with a dividend paid by the Issuer on awards previously granted and vest on the same terms as the awards to which they relate.

Read SEC document
December 11, 2025 Filed Dec 15, 2025 21:17 UTC
BENTLEY GREGORY SDirector · Executive Chair & President · 10% owner
GrantClass B Common Stock 3,958 $0.00 $0.00
Disclosure

SEC source: 0001104659-25-121148 · tm2532204-5_4seq1.xml · nonDerivative · entry 1

BENTLEY GREGORY S · CIK 0001214661 · Director · Executive Chair & President · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 7,595,601

F1 · kind: Represents dividend equivalent rights that accrued to the Reporting Person in connection with a dividend paid by the Issuer on awards previously granted and vest on the same terms as the awards to which they relate.

Read SEC document
December 11, 2025 Filed Dec 15, 2025 21:16 UTC
Shaman David R.Chief Legal Officer
GrantClass B Common Stock 460 $0.00 $0.00
Disclosure

SEC source: 0001104659-25-121147 · tm2532204-4_4seq1.xml · nonDerivative · entry 1

Shaman David R. · CIK 0001825193 · Chief Legal Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 640,150

F1 · kind: Represents dividend equivalent rights that accrued to the Reporting Person in connection with a dividend paid by the Issuer on awards previously granted and vest on the same terms as the awards to which they relate.

Read SEC document
December 11, 2025 Filed Dec 15, 2025 21:15 UTC
Ballard BrockChief Revenue Officer
GrantClass B Common Stock 78 $0.00 $0.00
Disclosure

SEC source: 0001104659-25-121143 · tm2532204-3_4seq1.xml · nonDerivative · entry 1

Ballard Brock · CIK 0001963448 · Chief Revenue Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 68,192

F1 · kind: Represents dividend equivalent rights that accrued to the Reporting Person in connection with a dividend paid by the Issuer on awards previously granted and vest on the same terms as the awards to which they relate.

Read SEC document
December 10, 2025 Filed Dec 12, 2025 21:15 UTC
Bentley Raymond B.Director · 10% owner
GiftClass B Common Stock 121,951 $0.00 $0.00
Disclosure

SEC source: 0001104659-25-120662 · tm2532204-2_4seq1.xml · nonDerivative · entry 1

Bentley Raymond B. · CIK 0001825229 · Director · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 15,101,853

Read SEC document
December 01, 2025 Filed Dec 3, 2025 23:52 UTC
BENTLEY GREGORY SDirector · Executive Chair & President · 10% owner
Tax withholdingClass B Common Stock 8,932 $41.85 $373,804.20
Disclosure

SEC source: 0001104659-25-118205 · tm2532204-1_4seq1.xml · nonDerivative · entry 1

BENTLEY GREGORY S · CIK 0001214661 · Director · Executive Chair & President · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 7,591,643

F1 · kind: Represents shares of Class B Common Stock withheld by the Issuer to cover taxes due by the Reporting Person upon a scheduled distribution of Class B Common Stock from the Issuer's Non-Qualified Deferred Compensation Plan.

Read SEC document
November 17, 2025 Filed Nov 19, 2025 21:15 UTC
Trimback Thomas FChief Accounting Officer
SaleClass B Common Stock 560 $43.02 $24,091.20
Disclosure

SEC source: 0001104659-25-114103 · tm2529520-3_4seq1.xml · nonDerivative · entry 1

Trimback Thomas F · CIK 0002015992 · Chief Accounting Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 13,806

Read SEC document
October 27, 2025 Filed Oct 28, 2025 20:15 UTC
Ballard BrockChief Revenue Officer
Tax withholdingClass B Common Stock 609 $52.20 $31,789.80
Disclosure

SEC source: 0001104659-25-103185 · tm2529520-2_4seq1.xml · nonDerivative · entry 1

Ballard Brock · CIK 0001963448 · Chief Revenue Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 68,114

F1 · kind: Represents shares withheld by the Issuer to cover taxes due by the Reporting Person upon the vesting of awards previously granted to the Reporting Person.

Read SEC document
October 25, 2025 Filed Oct 28, 2025 20:15 UTC
Trimback Thomas FChief Accounting Officer
Tax withholdingClass B Common Stock 74 $51.73 $3,828.02
Disclosure

SEC source: 0001104659-25-103183 · tm2529520-1_4seq1.xml · nonDerivative · entry 1

Trimback Thomas F · CIK 0002015992 · Chief Accounting Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 14,366

F1 · kind: Represents shares withheld by the Issuer to cover taxes due by the Reporting Person upon the vesting of awards previously granted to the Reporting Person.

Read SEC document
October 22, 2025 Filed Oct 24, 2025 20:15 UTC
BENTLEY GREGORY SDirector · Executive Chair & President · 10% owner
Tax withholdingClass B Common Stock 13,181 $52.01 $685,543.81
Disclosure

SEC source: 0001104659-25-102140 · tm2526753-13_4seq1.xml · nonDerivative · entry 2

BENTLEY GREGORY S · CIK 0001214661 · Director · Executive Chair & President · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 7,600,575

F2 · kind: Represents shares withheld by the Issuer to cover taxes owed by the Reporting Person in respect of the Bonus Pool Payment.

Read SEC document
October 22, 2025 Filed Oct 24, 2025 20:15 UTC
BENTLEY GREGORY SDirector · Executive Chair & President · 10% owner
GrantClass B Common Stock 30,135 $52.01 $1,567,321.35
Disclosure

SEC source: 0001104659-25-102140 · tm2526753-13_4seq1.xml · nonDerivative · entry 1

BENTLEY GREGORY S · CIK 0001214661 · Director · Executive Chair & President · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 7,613,756

F1 · kind: Represents the stock portion of compensation paid to the Reporting Person pursuant to the Issuer's Bonus Pool Plan (the "Bonus Pool Payment").

Read SEC document
September 30, 2025 Filed Oct 2, 2025 20:22 UTC
Andre WernerChief Financial Officer
GrantClass B Common Stock 125 $0.00 $0.00
Disclosure

SEC source: 0001104659-25-096086 · tm2526753-12_4seq1.xml · nonDerivative · entry 1

Andre Werner · CIK 0001825257 · Chief Financial Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 351,206

F1 · kind: Represents dividend equivalent rights that accrued to the Reporting Person in connection with a dividend paid by the Issuer on awards previously granted and vest on the same terms as the awards to which they relate.

F2 · balance_after: Includes shares of Class B Common Stock acquired by the Reporting Person through the Bentley Systems, Incorporated Global Employee Stock Purchase Plan for an offering period ended on June 30, 2025 for which the Reporting Person's enrollment and contribution elections were made in December 2024.

Read SEC document
September 30, 2025 Filed Oct 2, 2025 20:21 UTC
Trimback Thomas FChief Accounting Officer
GrantClass B Common Stock 13 $0.00 $0.00
Disclosure

SEC source: 0001104659-25-096085 · tm2526753-11_4seq1.xml · nonDerivative · entry 1

Trimback Thomas F · CIK 0002015992 · Chief Accounting Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 14,440

F1 · kind: Represents dividend equivalent rights that accrued to the Reporting Person in connection with a dividend paid by the Issuer on awards previously granted and vest on the same terms as the awards to which they relate.

Read SEC document
September 30, 2025 Filed Oct 2, 2025 20:21 UTC
Bentley Raymond B.Director · 10% owner
GrantClass B Common Stock 1,380 $0.00 $0.00
Disclosure

SEC source: 0001104659-25-096084 · tm2526753-10_4seq1.xml · nonDerivative · entry 1

Bentley Raymond B. · CIK 0001825229 · Director · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 15,348,804

F1 · kind: Represents dividend equivalent rights that accrued to the Reporting Person in connection with a dividend paid by the Issuer on awards previously granted and vest on the same terms as the awards to which they relate.

Read SEC document
September 30, 2025 Filed Oct 2, 2025 20:20 UTC
Cumins NicholasDirector · Chief Executive Officer
GrantClass B Common Stock 387 $0.00 $0.00
Disclosure

SEC source: 0001104659-25-096083 · tm2526753-9_4seq1.xml · nonDerivative · entry 1

Cumins Nicholas · CIK 0001896877 · Director · Chief Executive Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 439,789

F1 · kind: Represents dividend equivalent rights that accrued to the Reporting Person in connection with a dividend paid by the Issuer on awards previously granted and vest on the same terms as the awards to which they relate.

Read SEC document
September 30, 2025 Filed Oct 2, 2025 20:19 UTC
Bentley Keith A.Director · 10% owner
GrantClass B Common Stock 1,024 $0.00 $0.00
Disclosure

SEC source: 0001104659-25-096081 · tm2526753-7_4seq1.xml · nonDerivative · entry 1

Bentley Keith A. · CIK 0001825187 · Director · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 3,960,351

F1 · kind: Represents dividend equivalent rights that accrued to the Reporting Person in connection with a dividend paid by the Issuer on awards previously granted and vest on the same terms as the awards to which they relate.

Read SEC document
September 30, 2025 Filed Oct 2, 2025 20:20 UTC GrantClass B Common Stock 68 $0.00 $0.00
Disclosure

SEC source: 0001104659-25-096082 · tm2526753-8_4seq1.xml · nonDerivative · entry 1

Griswold Kirk B. · CIK 0001825243 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 461,127

F1 · kind: Represents dividend equivalent rights that accrued to the Reporting Person in connection with a dividend paid by the Issuer on awards previously granted and vest on the same terms as the awards to which they relate.

Read SEC document
September 30, 2025 Filed Oct 2, 2025 20:19 UTC
Moutte JulienChief Technology Officer
GrantClass B Common Stock 58 $0.00 $0.00
Disclosure

SEC source: 0001104659-25-096080 · tm2526753-6_4seq1.xml · nonDerivative · entry 1

Moutte Julien · CIK 0002062214 · Chief Technology Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 68,903

F1 · kind: Represents dividend equivalent rights that accrued to the Reporting Person in connection with a dividend paid by the Issuer on awards previously granted and vest on the same terms as the awards to which they relate.

F2 · balance_after: Includes shares of Class B Common Stock acquired by the Reporting Person through the Bentley Systems, Incorporated Global Employee Stock Purchase Plan for an offering period ended on June 30, 2025 for which the Reporting Person's enrollment and contribution elections were made in December 2024.

Read SEC document
September 30, 2025 Filed Oct 2, 2025 20:18 UTC
Lee James KChief Operating Officer
GrantClass B Common Stock 211 $0.00 $0.00
Disclosure

SEC source: 0001104659-25-096079 · tm2526753-5_4seq1.xml · nonDerivative · entry 1

Lee James K · CIK 0002052647 · Chief Operating Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 172,192

F1 · kind: Represents dividend equivalent rights that accrued to the Reporting Person in connection with a dividend paid by the Issuer on awards previously granted and vest on the same terms as the awards to which they relate.

Read SEC document
September 30, 2025 Filed Oct 2, 2025 20:18 UTC
BENTLEY GREGORY SDirector · Executive Chair & President · 10% owner
GrantClass B Common Stock 3,185 $0.00 $0.00
Disclosure

SEC source: 0001104659-25-096078 · tm2526753-4_4seq1.xml · nonDerivative · entry 1

BENTLEY GREGORY S · CIK 0001214661 · Director · Executive Chair & President · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 7,583,621

F1 · kind: Represents dividend equivalent rights that accrued to the Reporting Person in connection with a dividend paid by the Issuer on awards previously granted and vest on the same terms as the awards to which they relate.

Read SEC document
September 30, 2025 Filed Oct 2, 2025 20:16 UTC
Shaman David R.Chief Legal Officer
GrantClass B Common Stock 367 $0.00 $0.00
Disclosure

SEC source: 0001104659-25-096074 · tm2526753-3_4seq1.xml · nonDerivative · entry 1

Shaman David R. · CIK 0001825193 · Chief Legal Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 639,690

F1 · kind: Represents dividend equivalent rights that accrued to the Reporting Person in connection with a dividend paid by the Issuer on awards previously granted and vest on the same terms as the awards to which they relate.

Read SEC document
September 30, 2025 Filed Oct 2, 2025 20:15 UTC
Bentley Barry J.Director · 10% owner
GrantClass B Common Stock 4 $0.00 $0.00
Disclosure

SEC source: 0001104659-25-096072 · tm2526753-2_4seq1.xml · nonDerivative · entry 1

Bentley Barry J. · CIK 0001825188 · Director · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 11,838,253

F1 · kind: Represents dividend equivalent rights that accrued to the Reporting Person in connection with a dividend paid by the Issuer on awards previously granted and vest on the same terms as the awards to which they relate.

Read SEC document
September 30, 2025 Filed Oct 2, 2025 20:15 UTC
Ballard BrockChief Revenue Officer
GrantClass B Common Stock 64 $0.00 $0.00
Disclosure

SEC source: 0001104659-25-096069 · tm2526753-1_4seq1.xml · nonDerivative · entry 1

Ballard Brock · CIK 0001963448 · Chief Revenue Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 68,723

F1 · kind: Represents dividend equivalent rights that accrued to the Reporting Person in connection with a dividend paid by the Issuer on awards previously granted and vest on the same terms as the awards to which they relate.

F2 · balance_after: Includes shares of Class B Common Stock acquired by the Reporting Person through the Bentley Systems, Incorporated Global Employee Stock Purchase Plan for an offering period ended on June 30, 2025 for which the Reporting Person's enrollment and contribution elections were made in December 2024.

Read SEC document
September 02, 2025 Filed Sep 4, 2025 20:15 UTC
Bentley Barry J.Director · 10% owner
GiftClass B Common Stock 110,000 $0.00 $0.00
Disclosure

SEC source: 0001104659-25-087474 · tm2524179-6_4seq1.xml · nonDerivative · entry 1

Bentley Barry J. · CIK 0001825188 · Director · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 11,838,249

Read SEC document
September 02, 2025 Filed Sep 4, 2025 20:15 UTC
BENTLEY GREGORY SDirector · Executive Chair & President · 10% owner
SaleClass B Common Stock 37,160 $54.83 $2,037,575.70
Disclosure

SEC source: 0001104659-25-087470 · tm2524179-5_4seq1.xml · nonDerivative · entry 1

BENTLEY GREGORY S · CIK 0001214661 · Director · Executive Chair & President · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 7,580,436

F1 · kind: Private sale to a family trust in satisfaction of a prior obligation.

Read SEC document
August 31, 2025 Filed Sep 3, 2025 20:15 UTC
Shaman David R.Chief Legal Officer
Tax withholdingClass B Common Stock 6,685 $55.03 $367,875.55
Disclosure

SEC source: 0001104659-25-087028 · tm2524179-4_4seq1.xml · nonDerivative · entry 1

Shaman David R. · CIK 0001825193 · Chief Legal Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 639,323

F1 · kind: Represents shares of Class B Common Stock withheld by the Issuer to cover taxes due by the Reporting Person upon a scheduled distribution of Class B Common Stock from the Issuer's Non-Qualified Deferred Compensation Plan.

F2 · price: Represents the volume weighted average price of the Issuer's Class B Common Stock as calculated pursuant to the Issuer's Non-Qualified Deferred Compensation Plan.

Read SEC document
August 27, 2025 Filed Aug 29, 2025 20:15 UTC
BENTLEY GREGORY SDirector · Executive Chair & President · 10% owner
GiftClass B Common Stock 351 $0.00 $0.00
Disclosure

SEC source: 0001104659-25-085674 · tm2524179-3_4seq1.xml · nonDerivative · entry 1

BENTLEY GREGORY S · CIK 0001214661 · Director · Executive Chair & President · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 7,617,596

Read SEC document
August 22, 2025 Filed Aug 26, 2025 20:23 UTC
Bentley Keith A.Director · 10% owner
GiftClass B Common Stock 100,000 $0.00 $0.00
Disclosure

SEC source: 0001104659-25-083101 · tm2524179-2_4seq1.xml · nonDerivative · entry 2

Bentley Keith A. · CIK 0001825187 · Director · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 3,959,327

F1 · kind: Represents a transfer of 100,000 shares of Class B Common Stock held by the Reporting Person's spouse individually to joint ownership with the Reporting Person. After giving effect to this transfer, the shares are reflected on this Form 4 as being owned directly by the Reporting Person.

Read SEC document
August 22, 2025 Filed Aug 26, 2025 20:23 UTC
Bentley Keith A.Director · 10% owner
GiftClass B Common Stock 100,000 $0.00 $0.00
Disclosure

SEC source: 0001104659-25-083101 · tm2524179-2_4seq1.xml · nonDerivative · entry 1

Bentley Keith A. · CIK 0001825187 · Director · 10% owner

10b5-1 filing: No plan indicated

Ownership: Indirect · By Spouse

Disclosed balance after: 0

F1 · kind: Represents a transfer of 100,000 shares of Class B Common Stock held by the Reporting Person's spouse individually to joint ownership with the Reporting Person. After giving effect to this transfer, the shares are reflected on this Form 4 as being owned directly by the Reporting Person.

Read SEC document
August 21, 2025 Filed Aug 25, 2025 20:15 UTC
BENTLEY GREGORY SDirector · Executive Chair & President · 10% owner
GiftClass B Common Stock 9,349 $0.00 $0.00
Disclosure

SEC source: 0001104659-25-082530 · tm2524179d1_4seq1.xml · nonDerivative · entry 1

BENTLEY GREGORY S · CIK 0001214661 · Director · Executive Chair & President · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 7,617,947

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August 01, 2025 Filed Aug 5, 2025 20:15 UTC
Shaman David R.Chief Legal Officer
Tax withholdingClass B Common Stock 1,201 $57.12 $68,601.12
Disclosure

SEC source: 0001104659-25-074191 · tm2521377-3_4seq1.xml · nonDerivative · entry 1

Shaman David R. · CIK 0001825193 · Chief Legal Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 646,008

F1 · kind: Represents shares of Class B Common Stock withheld by the Issuer to cover taxes due by the Reporting Person upon a scheduled distribution of Class B Common Stock from the Issuer's Non-Qualified Deferred Compensation Plan.

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July 29, 2025 Filed Jul 31, 2025 20:15 UTC
Shaman David R.Chief Legal Officer
SaleClass B Common Stock 400 $59.25 $23,700.00
Disclosure

SEC source: 0001104659-25-072700 · tm2521377-2_4seq1.xml · nonDerivative · entry 1

Shaman David R. · CIK 0001825193 · Chief Legal Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 647,209

F1 · kind: The sales reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on December 12, 2024.

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July 24, 2025 Filed Jul 28, 2025 20:15 UTC
BENTLEY GREGORY SDirector · Executive Chair & President · 10% owner
Tax withholdingClass B Common Stock 13,445 $58.35 $784,515.75
Disclosure

SEC source: 0001104659-25-071161 · tm2521377-1_4seq1.xml · nonDerivative · entry 2

BENTLEY GREGORY S · CIK 0001214661 · Director · Executive Chair & President · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 7,627,296

F2 · kind: Represents shares withheld by the Issuer to cover taxes owed by the Reporting Person in respect of the Bonus Pool Payment.

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July 24, 2025 Filed Jul 28, 2025 20:15 UTC
BENTLEY GREGORY SDirector · Executive Chair & President · 10% owner
GrantClass B Common Stock 30,737 $58.35 $1,793,503.95
Disclosure

SEC source: 0001104659-25-071161 · tm2521377-1_4seq1.xml · nonDerivative · entry 1

BENTLEY GREGORY S · CIK 0001214661 · Director · Executive Chair & President · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 7,640,741

F1 · kind: Represents the stock portion of compensation paid to the Reporting Person pursuant to the Issuer's Bonus Pool Plan (the "Bonus Pool Payment").

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July 14, 2025 Filed Jul 15, 2025 20:15 UTC
Shaman David R.Chief Legal Officer
SaleClass B Common Stock 19,348 $56.96 $1,102,104.65
Disclosure

SEC source: 0001104659-25-068097 · tm2518160-6_4seq1.xml · nonDerivative · entry 2

Shaman David R. · CIK 0001825193 · Chief Legal Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 647,609

F1 · kind: The sales reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on December 12, 2024.

F3 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions on July 14, 2025 at prices ranging from $56.92 to $57.05. The Reporting Person undertakes to provide to Bentley Systems, Incorporated, any security holder of Bentley Systems, Incorporated, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote.

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July 11, 2025 Filed Jul 15, 2025 20:15 UTC
Shaman David R.Chief Legal Officer
SaleClass B Common Stock 965 $56.92 $54,929.73
Disclosure

SEC source: 0001104659-25-068097 · tm2518160-6_4seq1.xml · nonDerivative · entry 1

Shaman David R. · CIK 0001825193 · Chief Legal Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 666,957

F1 · kind: The sales reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan adopted by the Reporting Person on December 12, 2024.

F2 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions on July 11, 2025 at prices ranging from $56.92 to $56.95. The Reporting Person undertakes to provide to Bentley Systems, Incorporated, any security holder of Bentley Systems, Incorporated, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the ranges set forth in this footnote.

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July 08, 2025 Filed Jul 10, 2025 20:15 UTC
Shaman David R.Chief Legal Officer
Tax withholdingClass B Common Stock 2,636 $55.90 $147,352.40
Disclosure

SEC source: 0001104659-25-066990 · tm2518160-5_4seq1.xml · nonDerivative · entry 1

Shaman David R. · CIK 0001825193 · Chief Legal Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 667,922

F1 · kind: Represents shares of Class B Common Stock withheld by the Issuer to cover taxes due by the Reporting Person upon a scheduled distribution of Class B Common Stock from the Issuer's Non-Qualified Deferred Compensation Plan.

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Value uses the disclosed total when available, otherwise shares × reported transaction price. It is not an estimate of exercise cash cost or investment performance.