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BENTLEY SYSTEMS INC

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438
SEC CIK
0001031308
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660

Last 12 months

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0 purchase rows · 2 sale rows

Disclosed non-derivative P/S rows, by transaction month. Includes amendments and private transactions.
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MonthPurchasesSales
Nov 202501
Dec 202500
Jan 202600
Feb 202600
Mar 202601
Apr 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
March 27, 2025 Filed Mar 31, 2025 20:17 UTC
BENTLEY GREGORY SDirector · Executive Chair & President · 10% owner
GrantClass B Common Stock 4,050 $0.00 $0.00
Disclosure

SEC source: 0001104659-25-029880 · tm259640-8_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: 7,758,279

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
March 27, 2025 Filed Mar 31, 2025 20:16 UTC
Bentley Barry J.Director · 10% owner
GrantClass B Common Stock 5 $0.00 $0.00
Disclosure

SEC source: 0001104659-25-029876 · tm259640-7_4seq1.xml · nonDerivative · entry 1

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 11,948,245

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
March 27, 2025 Filed Mar 31, 2025 20:15 UTC
Ballard BrockChief Revenue Officer
GrantClass B Common Stock 82 $0.00 $0.00
Disclosure

SEC source: 0001104659-25-029870 · tm259640-6_4seq1.xml · nonDerivative · entry 1

Ballard Brock · CIK 0001963448 · Chief Revenue Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 80,704

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
March 17, 2025 Filed Mar 19, 2025 20:17 UTC
Andre WernerChief Financial Officer
Tax withholdingClass B Common Stock 1,494 $42.43 $63,390.42
Disclosure

SEC source: 0001104659-25-025572 · tm259640-4_4seq1.xml · nonDerivative · entry 1

Andre Werner · CIK 0001825257 · Chief Financial Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 350,674

F1 · kind: Represents shares of Class B Common Stock 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
March 17, 2025 Filed Mar 19, 2025 20:16 UTC
Cumins NicholasDirector · Chief Executive Officer
Tax withholdingClass B Common Stock 2,142 $42.43 $90,885.06
Disclosure

SEC source: 0001104659-25-025570 · tm259640-3_4seq1.xml · nonDerivative · entry 1

Cumins Nicholas · CIK 0001896877 · Director · Chief Executive Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 439,672

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
March 17, 2025 Filed Mar 19, 2025 20:15 UTC
Shaman David R.Chief Legal Officer
Tax withholdingClass B Common Stock 1,165 $42.43 $49,430.95
Disclosure

SEC source: 0001104659-25-025569 · tm259640-2_4seq1.xml · nonDerivative · entry 2

Shaman David R. · CIK 0001825193 · Chief Legal Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 699,402

F1 · kind: Represents shares of Class B Common Stock 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
March 17, 2025 Filed Mar 19, 2025 20:15 UTC
Shaman David R.Chief Legal Officer
GiftClass B Common Stock 9,764 $0.00 $0.00
Disclosure

SEC source: 0001104659-25-025569 · tm259640-2_4seq1.xml · nonDerivative · entry 1

Shaman David R. · CIK 0001825193 · Chief Legal Officer

10b5-1 filing: No plan indicated

Ownership: Indirect · By Grantor Retained Annuity Trusts

Disclosed balance after: 279,308

Read SEC document
March 17, 2025 Filed Mar 19, 2025 20:15 UTC
Ballard BrockChief Revenue Officer
Tax withholdingClass B Common Stock 193 $42.43 $8,188.99
Disclosure

SEC source: 0001104659-25-025568 · tm259640-1_4seq1.xml · nonDerivative · entry 1

Ballard Brock · CIK 0001963448 · Chief Revenue Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 80,622

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
March 13, 2025 Filed Mar 17, 2025 20:17 UTC
Shaman David R.Chief Legal Officer
Tax withholdingClass B Common Stock 2,691 $40.11 $107,936.01
Disclosure

SEC source: 0001104659-25-024431 · tm256909-8_4seq1.xml · nonDerivative · entry 2

Shaman David R. · CIK 0001825193 · Chief Legal Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 719,761

F2 · kind: Represents shares of Class B Common Stock 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
March 13, 2025 Filed Mar 17, 2025 20:17 UTC
Shaman David R.Chief Legal Officer
GrantClass B Common Stock 18,148 $0.00 $0.00
Disclosure

SEC source: 0001104659-25-024431 · tm256909-8_4seq1.xml · nonDerivative · entry 1

Shaman David R. · CIK 0001825193 · Chief Legal Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 722,452

F1 · kind: Represents a time-based restricted stock unit award granted pursuant to the Issuer's 2020 Omnibus Incentive Plan which vests over four years with one-quarter of such award vesting on each grant date anniversary.

Read SEC document
March 13, 2025 Filed Mar 17, 2025 20:16 UTC
Ballard BrockChief Revenue Officer
Tax withholdingClass B Common Stock 1,881 $40.11 $75,446.91
Disclosure

SEC source: 0001104659-25-024430 · tm256909-7_4seq1.xml · nonDerivative · entry 2

Ballard Brock · CIK 0001963448 · Chief Revenue Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 80,815

F2 · 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
March 13, 2025 Filed Mar 17, 2025 20:16 UTC
Ballard BrockChief Revenue Officer
GrantClass B Common Stock 17,054 $0.00 $0.00
Disclosure

SEC source: 0001104659-25-024430 · tm256909-7_4seq1.xml · nonDerivative · entry 1

Ballard Brock · CIK 0001963448 · Chief Revenue Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 82,696

F1 · kind: Represents a time-based restricted stock unit award granted pursuant to the Issuer's 2020 Omnibus Incentive Plan which vests over four years with one-quarter of such award vesting on each grant date anniversary.

Read SEC document
March 13, 2025 Filed Mar 17, 2025 20:16 UTC
Andre WernerChief Financial Officer
Tax withholdingClass B Common Stock 3,085 $40.11 $123,739.35
Disclosure

SEC source: 0001104659-25-024428 · tm256909-6_4seq1.xml · nonDerivative · entry 2

Andre Werner · CIK 0001825257 · Chief Financial Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 352,168

F2 · kind: Represents shares of Class B Common Stock 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
March 13, 2025 Filed Mar 17, 2025 20:16 UTC
Andre WernerChief Financial Officer
GrantClass B Common Stock 20,314 $0.00 $0.00
Disclosure

SEC source: 0001104659-25-024428 · tm256909-6_4seq1.xml · nonDerivative · entry 1

Andre Werner · CIK 0001825257 · Chief Financial Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 355,253

F1 · kind: Represents a time-based restricted stock unit award granted pursuant to the Issuer's 2020 Omnibus Incentive Plan which vests over four years with one-quarter of such award vesting on each grant date anniversary.

Read SEC document
March 13, 2025 Filed Mar 17, 2025 20:15 UTC
Trimback Thomas FChief Accounting Officer
Tax withholdingClass B Common Stock 193 $40.11 $7,741.23
Disclosure

SEC source: 0001104659-25-024427 · tm256909-5_4seq1.xml · nonDerivative · entry 2

Trimback Thomas F · CIK 0002015992 · Chief Accounting Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 14,565

F2 · 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
March 13, 2025 Filed Mar 17, 2025 20:15 UTC
Trimback Thomas FChief Accounting Officer
GrantClass B Common Stock 3,591 $0.00 $0.00
Disclosure

SEC source: 0001104659-25-024427 · tm256909-5_4seq1.xml · nonDerivative · entry 1

Trimback Thomas F · CIK 0002015992 · Chief Accounting Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 14,758

F1 · kind: Represents a time-based restricted stock unit award granted pursuant to the Issuer's 2020 Omnibus Incentive Plan which vests over four years with one-quarter of such award vesting on each grant date anniversary.

Read SEC document
March 13, 2025 Filed Mar 17, 2025 20:15 UTC
Cumins NicholasDirector · Chief Executive Officer
Tax withholdingClass B Common Stock 3,572 $40.11 $143,272.92
Disclosure

SEC source: 0001104659-25-024423 · tm256909-4_4seq1.xml · nonDerivative · entry 3

Cumins Nicholas · CIK 0001896877 · Director · Chief Executive Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 441,814

F3 · 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
March 13, 2025 Filed Mar 17, 2025 20:15 UTC
Cumins NicholasDirector · Chief Executive Officer
GrantClass B Common Stock 24,122 $0.00 $0.00
Disclosure

SEC source: 0001104659-25-024423 · tm256909-4_4seq1.xml · nonDerivative · entry 2

Cumins Nicholas · CIK 0001896877 · Director · Chief Executive Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 445,386

F2 · kind: Represents a time-based restricted stock unit award granted pursuant to the Issuer's 2020 Omnibus Incentive Plan which vests over four years with one-quarter of such award vesting on each grant date anniversary.

Read SEC document
March 13, 2025 Filed Mar 17, 2025 20:15 UTC
Cumins NicholasDirector · Chief Executive Officer
GrantClass B Common Stock 28,913 $0.00 $0.00
Disclosure

SEC source: 0001104659-25-024423 · tm256909-4_4seq1.xml · nonDerivative · entry 1

Cumins Nicholas · CIK 0001896877 · Director · Chief Executive Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 421,264

F1 · kind: Represents a time-based restricted stock unit award granted pursuant to the Issuer's Career Stock Program which vests on December 15, 2029.

Read SEC document
March 13, 2025 Filed Mar 17, 2025 20:15 UTC
Lee James KChief Operating Officer
GrantClass B Common Stock 12,189 $0.00 $0.00
Disclosure

SEC source: 0001104659-25-024421 · tm256909-3_4seq1.xml · nonDerivative · entry 1

Lee James K · CIK 0002052647 · Chief Operating Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 177,533

F1 · kind: Represents a time-based restricted stock unit award granted pursuant to the Issuer's 2020 Omnibus Incentive Plan which vests over four years with one-quarter of such award vesting on each grant date anniversary.

Read SEC document
March 12, 2025 Filed Mar 14, 2025 20:15 UTC
BENTLEY GREGORY SDirector · Executive Chair & President · 10% owner
GiftClass B Common Stock 605 $0.00 $0.00
Disclosure

SEC source: 0001104659-25-023964 · tm256909-2_4seq1.xml · nonDerivative · entry 3

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

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 7,754,229

Read SEC document
March 12, 2025 Filed Mar 14, 2025 20:15 UTC
BENTLEY GREGORY SDirector · Executive Chair & President · 10% owner
GiftClass B Common Stock 605 $0.00 $0.00
Disclosure

SEC source: 0001104659-25-023964 · tm256909-2_4seq1.xml · nonDerivative · entry 2

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

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 7,754,834

Read SEC document
March 12, 2025 Filed Mar 14, 2025 20:15 UTC
BENTLEY GREGORY SDirector · Executive Chair & President · 10% owner
SaleClass B Common Stock 53,968 $41.04 $2,214,803.55
Disclosure

SEC source: 0001104659-25-023964 · tm256909-2_4seq1.xml · nonDerivative · entry 1

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

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 7,755,439

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 10, 2024.

F2 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions on March 12, 2025 at prices ranging from $40.70 to $41.695. 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.

Read SEC document
March 03, 2025 Filed Mar 5, 2025 21:15 UTC
Ballard BrockChief Revenue Officer
SaleClass B Common Stock 1,548 $43.78 $67,775.16
Disclosure

SEC source: 0001104659-25-020881 · tm256909-1_4seq1.xml · nonDerivative · entry 2

Ballard Brock · CIK 0001963448 · Chief Revenue Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 65,642

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 November 19, 2024.

F3 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions on March 3, 2025 at prices ranging from $43.60 to $44.5999. 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.

Read SEC document
March 03, 2025 Filed Mar 5, 2025 21:15 UTC
Ballard BrockChief Revenue Officer
SaleClass B Common Stock 6,136 $43.13 $264,646.29
Disclosure

SEC source: 0001104659-25-020881 · tm256909-1_4seq1.xml · nonDerivative · entry 1

Ballard Brock · CIK 0001963448 · Chief Revenue Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 67,190

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 November 19, 2024.

F2 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions on March 3, 2025 at prices ranging from $42.56 to $43.5599. 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.

Read SEC document
January 31, 2025 Filed Feb 4, 2025 21:17 UTC
Shaman David R.Chief Legal Officer
Tax withholdingClass B Common Stock 20,135 $46.55 $937,284.25
Disclosure

SEC source: 0001104659-25-009120 · tm255350-3_4seq1.xml · nonDerivative · entry 3

Shaman David R. · CIK 0001825193 · Chief Legal Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 704,304

F3 · kind: Represents shares withheld by the Issuer to cover taxes upon the vesting of performance-based restricted stock units previously granted to the Reporting Person.

Read SEC document
January 31, 2025 Filed Feb 4, 2025 21:17 UTC
Shaman David R.Chief Legal Officer
GrantClass B Common Stock 46,297 $46.55 $2,155,125.35
Disclosure

SEC source: 0001104659-25-009120 · tm255350-3_4seq1.xml · nonDerivative · entry 2

Shaman David R. · CIK 0001825193 · Chief Legal Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 724,439

F2 · kind: Represents shares acquired upon the vesting of performance-based restricted stock units previously granted to the Reporting Person.

Read SEC document
January 31, 2025 Filed Feb 4, 2025 21:17 UTC
Shaman David R.Chief Legal Officer
Tax withholdingClass B Common Stock 19,060 $46.55 $887,243.00
Disclosure

SEC source: 0001104659-25-009120 · tm255350-3_4seq1.xml · nonDerivative · entry 1

Shaman David R. · CIK 0001825193 · Chief Legal Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 678,142

F1 · kind: Represents shares of Class B Common Stock 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
January 31, 2025 Filed Feb 4, 2025 21:16 UTC
Andre WernerChief Financial Officer
Tax withholdingClass B Common Stock 10,068 $46.55 $468,665.40
Disclosure

SEC source: 0001104659-25-009116 · tm255350-2_4seq1.xml · nonDerivative · entry 3

Andre Werner · CIK 0001825257 · Chief Financial Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 334,939

F3 · kind: Represents shares withheld by the Issuer to cover taxes upon the vesting of performance-based restricted stock units previously granted to the Reporting Person.

Read SEC document
January 31, 2025 Filed Feb 4, 2025 21:16 UTC
Andre WernerChief Financial Officer
GrantClass B Common Stock 23,148 $46.55 $1,077,539.40
Disclosure

SEC source: 0001104659-25-009116 · tm255350-2_4seq1.xml · nonDerivative · entry 2

Andre Werner · CIK 0001825257 · Chief Financial Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 345,007

F2 · kind: Represents shares acquired upon the vesting of performance-based restricted stock units previously granted to the Reporting Person.

Read SEC document
January 31, 2025 Filed Feb 4, 2025 21:16 UTC
Andre WernerChief Financial Officer
Tax withholdingClass B Common Stock 9,119 $46.55 $424,489.45
Disclosure

SEC source: 0001104659-25-009116 · tm255350-2_4seq1.xml · nonDerivative · entry 1

Andre Werner · CIK 0001825257 · Chief Financial Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 321,859

F1 · kind: Represents shares of Class B Common Stock 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
January 31, 2025 Filed Feb 4, 2025 21:15 UTC
Cumins NicholasDirector · Chief Executive Officer
Tax withholdingClass B Common Stock 35,733 $46.55 $1,663,371.15
Disclosure

SEC source: 0001104659-25-009113 · tm255350-1_4seq1.xml · nonDerivative · entry 3

Cumins Nicholas · CIK 0001896877 · Director · Chief Executive Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 392,351

F3 · kind: Represents shares withheld by the Issuer to cover taxes upon the vesting of performance-based restricted stock units previously granted to the Reporting Person.

Read SEC document
January 31, 2025 Filed Feb 4, 2025 21:15 UTC
Cumins NicholasDirector · Chief Executive Officer
GrantClass B Common Stock 77,161 $46.55 $3,591,844.55
Disclosure

SEC source: 0001104659-25-009113 · tm255350-1_4seq1.xml · nonDerivative · entry 2

Cumins Nicholas · CIK 0001896877 · Director · Chief Executive Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 428,084

F2 · kind: Represents shares acquired upon the vesting of performance-based restricted stock units previously granted to the Reporting Person.

Read SEC document
January 31, 2025 Filed Feb 4, 2025 21:15 UTC
Cumins NicholasDirector · Chief Executive Officer
Tax withholdingClass B Common Stock 36,145 $46.55 $1,682,549.75
Disclosure

SEC source: 0001104659-25-009113 · tm255350-1_4seq1.xml · nonDerivative · entry 1

Cumins Nicholas · CIK 0001896877 · Director · Chief Executive Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 350,923

F1 · kind: Represents shares of Class B Common Stock 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
January 30, 2025 Filed Feb 3, 2025 21:15 UTC
Trimback Thomas FChief Accounting Officer
Tax withholdingClass B Common Stock 294 $45.92 $13,500.48
Disclosure

SEC source: 0001104659-25-008627 · tm255053d1_4seq1.xml · nonDerivative · entry 1

Trimback Thomas F · CIK 0002015992 · Chief Accounting Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 11,167

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
January 24, 2025 Filed Jan 28, 2025 21:15 UTC
Bentley Keith A.Director · 10% owner
SaleClass B Common Stock 1,152 $46.33 $53,369.86
Disclosure

SEC source: 0001104659-25-006704 · tm254565-1_4seq1.xml · nonDerivative · entry 1

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

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 16,703,876

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 September 6, 2024.

F2 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions on January 24, 2025 at prices ranging from $46.18 to $46.45. 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.

Read SEC document
January 22, 2025 Filed Jan 23, 2025 21:15 UTC
Lee James KChief Operating Officer
GrantClass B Common Stock 165,344 $0.00 $0.00
Disclosure

SEC source: 0001104659-25-005618 · tm254119-2_4seq1.xml · nonDerivative · entry 1

Lee James K · CIK 0002052647 · Chief Operating Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 165,344

F1 · kind: Represents a time-based restricted stock unit award granted pursuant to the Issuer's 2020 Omnibus Incentive Plan which vests 14% on May 13, 2025, 14% on December 15, 2025 and 18% on each of December 15, 2026, 2027, 2028 and 2029.

Read SEC document
January 22, 2025 Filed Jan 24, 2025 21:19 UTC
Andre WernerChief Financial Officer
Tax withholdingClass B Common Stock 4,228 $46.56 $196,855.68
Disclosure

SEC source: 0001104659-25-006007 · tm254119-8_4seq1.xml · nonDerivative · entry 2

Andre Werner · CIK 0001825257 · Chief Financial Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 330,978

F2 · kind: Represents shares withheld by the Issuer to cover taxes upon the vesting of performance-based restricted stock units previously granted to the Reporting Person.

Read SEC document
January 22, 2025 Filed Jan 24, 2025 21:19 UTC
Andre WernerChief Financial Officer
GrantClass B Common Stock 14,258 $46.56 $663,852.48
Disclosure

SEC source: 0001104659-25-006007 · tm254119-8_4seq1.xml · nonDerivative · entry 1

Andre Werner · CIK 0001825257 · Chief Financial Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 335,206

F1 · kind: Represents shares acquired upon the vesting of performance-based restricted stock units previously granted to the Reporting Person.

Read SEC document
January 22, 2025 Filed Jan 24, 2025 21:18 UTC
Trimback Thomas FChief Accounting Officer
Tax withholdingClass B Common Stock 976 $46.56 $45,442.56
Disclosure

SEC source: 0001104659-25-006006 · tm254119-7_4seq1.xml · nonDerivative · entry 2

Trimback Thomas F · CIK 0002015992 · Chief Accounting Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 11,461

F2 · kind: Represents shares withheld by the Issuer to cover taxes upon the vesting of performance-based restricted stock units previously granted to the Reporting Person.

Read SEC document
January 22, 2025 Filed Jan 24, 2025 21:18 UTC
Trimback Thomas FChief Accounting Officer
GrantClass B Common Stock 2,888 $46.56 $134,465.28
Disclosure

SEC source: 0001104659-25-006006 · tm254119-7_4seq1.xml · nonDerivative · entry 1

Trimback Thomas F · CIK 0002015992 · Chief Accounting Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 12,437

F1 · kind: Represents shares acquired upon the vesting of performance-based restricted stock units previously granted to the Reporting Person.

Read SEC document
January 22, 2025 Filed Jan 24, 2025 21:17 UTC
Cumins NicholasDirector · Chief Executive Officer
Tax withholdingClass B Common Stock 8,168 $46.56 $380,302.08
Disclosure

SEC source: 0001104659-25-006003 · tm254119-6_4seq1.xml · nonDerivative · entry 2

Cumins Nicholas · CIK 0001896877 · Director · Chief Executive Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 387,068

F2 · kind: Represents shares withheld by the Issuer to cover taxes upon the vesting of performance-based restricted stock units previously granted to the Reporting Person.

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January 22, 2025 Filed Jan 24, 2025 21:17 UTC
Cumins NicholasDirector · Chief Executive Officer
GrantClass B Common Stock 19,633 $46.56 $914,112.48
Disclosure

SEC source: 0001104659-25-006003 · tm254119-6_4seq1.xml · nonDerivative · entry 1

Cumins Nicholas · CIK 0001896877 · Director · Chief Executive Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 395,236

F1 · kind: Represents shares acquired upon the vesting of performance-based restricted stock units previously granted to the Reporting Person.

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January 22, 2025 Filed Jan 24, 2025 21:16 UTC
BENTLEY GREGORY SDirector · Executive Chair & President · 10% owner
GrantClass B Common Stock 22,818 $46.56 $1,062,406.08
Disclosure

SEC source: 0001104659-25-006000 · tm254119-5_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: 7,809,407

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

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January 22, 2025 Filed Jan 24, 2025 21:15 UTC
Shaman David R.Chief Legal Officer
Tax withholdingClass B Common Stock 3,802 $46.56 $177,021.12
Disclosure

SEC source: 0001104659-25-005998 · tm254119-4_4seq1.xml · nonDerivative · entry 2

Shaman David R. · CIK 0001825193 · Chief Legal Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 697,202

F2 · kind: Represents shares withheld by the Issuer to cover taxes upon the vesting of performance-based restricted stock units previously granted to the Reporting Person.

F3 · 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 December 31, 2024 for which the Reporting Person's enrollment and contribution elections were made in June 2024.

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January 22, 2025 Filed Jan 24, 2025 21:15 UTC
Shaman David R.Chief Legal Officer
GrantClass B Common Stock 12,738 $46.56 $593,081.28
Disclosure

SEC source: 0001104659-25-005998 · tm254119-4_4seq1.xml · nonDerivative · entry 1

Shaman David R. · CIK 0001825193 · Chief Legal Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 700,885

F1 · kind: Represents shares acquired upon the vesting of performance-based restricted stock units previously granted to the Reporting Person.

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January 22, 2025 Filed Jan 24, 2025 21:15 UTC
Ballard BrockChief Revenue Officer
Tax withholdingClass B Common Stock 2,966 $46.56 $138,096.96
Disclosure

SEC source: 0001104659-25-005993 · tm254119-3_4seq1.xml · nonDerivative · entry 2

Ballard Brock · CIK 0001963448 · Chief Revenue Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 73,326

F2 · kind: Represents shares withheld by the Issuer to cover taxes upon the vesting of performance-based restricted stock units previously granted to the Reporting Person.

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January 22, 2025 Filed Jan 24, 2025 21:15 UTC
Ballard BrockChief Revenue Officer
GrantClass B Common Stock 10,244 $46.56 $476,960.64
Disclosure

SEC source: 0001104659-25-005993 · tm254119-3_4seq1.xml · nonDerivative · entry 1

Ballard Brock · CIK 0001963448 · Chief Revenue Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 76,292

F1 · kind: Represents shares acquired upon the vesting of performance-based restricted stock units previously granted to the Reporting Person.

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January 02, 2025 Filed Jan 6, 2025 21:17 UTC
Ballard BrockChief Revenue Officer
Tax withholdingClass B Common Stock 2,171 $46.70 $101,385.70
Disclosure

SEC source: 0001104659-25-001323 · tm251966-2_4seq1.xml · nonDerivative · entry 1

Ballard Brock · CIK 0001963448 · Chief Revenue Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 66,048

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.

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 December 31, 2024 for which the Reporting Person's enrollment and contribution elections were made in June 2024.

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January 02, 2025 Filed Jan 6, 2025 21:16 UTC
Bentley Keith A.Director · 10% owner
SaleClass B Common Stock 69,573 $46.67 $3,246,811.89
Disclosure

SEC source: 0001104659-25-001322 · tm251966-1_4seq1.xml · nonDerivative · entry 1

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

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 16,705,028

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 September 6, 2024.

F2 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions on January 2, 2025 at prices ranging from $46.28 to $47.24. 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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Value uses the disclosed total when available, otherwise shares × reported transaction price. It is not an estimate of exercise cash cost or investment performance.