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Bentley Raymond B.

Disclosed activity across 1 company

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38310
SEC CIK
0001825229

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Reported relationships

Latest disclosed role at each company.

CompanyLast reported asReport datePublished
BENTLEY SYSTEMS INCBSY · Entity 438Director · 10% ownerSeptember 29, 2026October 02, 2026

Disclosed balances

About these balances

Latest available filing per company, not a reconstructed current portfolio. Matching sequences show the last reported balance with all source rows expandable; grouping alone does not establish account ownership. Do not add unresolved positions together. Filings may omit unchanged positions, and amendments may correct only part of an older disclosure. Jointly reported shares are not necessarily this owner's personal holdings.

BENTLEY SYSTEMS INC

Report date September 29, 2026 · Filed October 02, 2026

Security / awardOwnership accountDisclosed shares / unitsDisclosure context
Class B Common StockSEC Table I · non-derivativeDirect14,816,404 Reported balance After 2026-09-29 transaction · row 1
1 source row

Row 1 · 2026-09-29 · Grant · Acquired 2,044 · Balance 14,816,404

F1: 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.

Class B Common StockSEC Table I · non-derivativeIndirectBy Spouse125,000 Reported balance Holding disclosure · report date 2026-09-29 · row 2 Holding and transaction disclosures are not merged.
1 source row

Row 2 · Balance 125,000

Class B Common StockSEC Table I · non-derivativeIndirectBy 401(K) Plan92,654 Reported balance Holding disclosure · report date 2026-09-29 · row 3 Holding and transaction disclosures are not merged.
1 source row

Row 3 · Balance 92,654

Filing footnotes · ownership attribution and instrument terms

F1: 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.

Transaction history

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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 dateCompanyActivity / securityShares / unitsReported priceReported valueDetails
April 21, 2022 Filed Apr 22, 2022 20:52 UTC BENTLEY SYSTEMS INC BSY · Entity 438 SaleClass B Common Stock 140,002 $43.46 $6,084,934.93
Disclosure

SEC source: 0001104659-22-049053 · tm2213180-8_4seq1.xml · nonDerivative · entry 3

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

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 18,145,121

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 March 14, 2022.

F4 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions on April 21, 2022 at prices ranging from $43.0600 to $44.0500. 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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April 20, 2022 Filed Apr 22, 2022 20:52 UTC BENTLEY SYSTEMS INC BSY · Entity 438 SaleClass B Common Stock 6,349 $44.36 $281,614.34
Disclosure

SEC source: 0001104659-22-049053 · tm2213180-8_4seq1.xml · nonDerivative · entry 2

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

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 18,285,123

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 March 14, 2022.

F3 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions on April 20, 2022 at prices ranging from $44.2600 to $44.5350. 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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April 20, 2022 Filed Apr 22, 2022 20:52 UTC BENTLEY SYSTEMS INC BSY · Entity 438 SaleClass B Common Stock 138,305 $43.59 $6,028,687.29
Disclosure

SEC source: 0001104659-22-049053 · tm2213180-8_4seq1.xml · nonDerivative · entry 1

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

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 18,291,472

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 March 14, 2022.

F2 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions on April 20, 2022 at prices ranging from $43.1750 to $44.1600. 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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March 15, 2022 Filed Mar 17, 2022 21:34 UTC BENTLEY SYSTEMS INC BSY · Entity 438 GrantClass B Common Stock 941 $0.00 $0.00
Disclosure

SEC source: 0001104659-22-035140 · tm229604-9_4seq1.xml · nonDerivative · entry 1

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

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 18,429,777

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 16, 2021 Filed Dec 20, 2021 21:50 UTC BENTLEY SYSTEMS INC BSY · Entity 438 GrantClass B Common Stock 708 $0.00 $0.00
Disclosure

SEC source: 0001104659-21-151750 · tm2135906-9_4seq1.xml · nonDerivative · entry 3

Bentley Raymond B. · CIK 0001825229 · Director · Executive Vice President · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 18,428,836

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
November 15, 2021 Filed Dec 20, 2021 21:50 UTC BENTLEY SYSTEMS INC BSY · Entity 438 GiftClass B Common Stock 500 $0.00 $0.00
Disclosure

SEC source: 0001104659-21-151750 · tm2135906-9_4seq1.xml · nonDerivative · entry 2

Bentley Raymond B. · CIK 0001825229 · Director · Executive Vice President · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 18,428,128

Read SEC document
September 09, 2021 Filed Sep 13, 2021 20:53 UTC BENTLEY SYSTEMS INC BSY · Entity 438 GrantClass B Common Stock 480 $0.00 $0.00
Disclosure

SEC source: 0001104659-21-115134 · tm2127458d7_4.xml · nonDerivative · entry 1

Bentley Raymond B. · CIK 0001825229 · Director · Executive Vice President · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 18,928,628

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
August 17, 2021 Filed Dec 20, 2021 21:50 UTC BENTLEY SYSTEMS INC BSY · Entity 438 GiftClass B Common Stock 500,000 $0.00 $0.00
Disclosure

SEC source: 0001104659-21-151750 · tm2135906-9_4seq1.xml · nonDerivative · entry 1

Bentley Raymond B. · CIK 0001825229 · Director · Executive Vice President · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 18,428,628

Read SEC document
August 03, 2021 Filed Aug 4, 2021 20:11 UTC BENTLEY SYSTEMS INC BSY · Entity 438 SaleClass B Common Stock 4,937 $61.18 $302,025.42
Disclosure

SEC source: 0001104659-21-100075 · tm2123836-3_4seq1.xml · nonDerivative · entry 1

Bentley Raymond B. · CIK 0001825229 · Director · Executive Vice President · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 18,928,148

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 June 11, 2021.

F2 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions on August 3, 2021 at prices ranging from $60.91 to $61.30. 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
August 02, 2021 Filed Aug 3, 2021 20:10 UTC BENTLEY SYSTEMS INC BSY · Entity 438 SaleClass B Common Stock 2,172 $61.36 $133,273.27
Disclosure

SEC source: 0001104659-21-099451 · tm2123836-2_4seq1.xml · nonDerivative · entry 3

Bentley Raymond B. · CIK 0001825229 · Director · Executive Vice President · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 18,933,085

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 June 11, 2021.

F4 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions on August 2, 2021 at prices ranging from $61.335 to $61.42. 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
August 02, 2021 Filed Aug 3, 2021 20:10 UTC BENTLEY SYSTEMS INC BSY · Entity 438 SaleClass B Common Stock 77,158 $61.05 $4,710,140.97
Disclosure

SEC source: 0001104659-21-099451 · tm2123836-2_4seq1.xml · nonDerivative · entry 2

Bentley Raymond B. · CIK 0001825229 · Director · Executive Vice President · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 18,935,257

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 June 11, 2021.

F3 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions on August 2, 2021 at prices ranging from $60.335 to $61.33. 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
July 30, 2021 Filed Aug 3, 2021 20:10 UTC BENTLEY SYSTEMS INC BSY · Entity 438 SaleClass B Common Stock 51,239 $60.83 $3,117,068.20
Disclosure

SEC source: 0001104659-21-099451 · tm2123836-2_4seq1.xml · nonDerivative · entry 1

Bentley Raymond B. · CIK 0001825229 · Director · Executive Vice President · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 19,012,415

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 June 11, 2021.

F2 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions on July 30, 2021 at prices ranging from $60.43 to $61.23. 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
July 29, 2021 Filed Jul 30, 2021 20:11 UTC BENTLEY SYSTEMS INC BSY · Entity 438 SaleClass B Common Stock 28,129 $61.39 $1,726,743.67
Disclosure

SEC source: 0001104659-21-098247 · tm2121736-11_4seq1.xml · nonDerivative · entry 3

Bentley Raymond B. · CIK 0001825229 · Director · Executive Vice President · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 19,063,654

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 June 11, 2021.

F4 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions on July 29, 2021 at prices ranging from $61.04 to $61.84. 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
July 29, 2021 Filed Jul 30, 2021 20:11 UTC BENTLEY SYSTEMS INC BSY · Entity 438 SaleClass B Common Stock 17,757 $60.91 $1,081,578.87
Disclosure

SEC source: 0001104659-21-098247 · tm2121736-11_4seq1.xml · nonDerivative · entry 2

Bentley Raymond B. · CIK 0001825229 · Director · Executive Vice President · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 19,091,783

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 June 11, 2021.

F3 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions on July 29, 2021 at prices ranging from $60.04 to $61.03. 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
July 28, 2021 Filed Jul 30, 2021 20:11 UTC BENTLEY SYSTEMS INC BSY · Entity 438 SaleClass B Common Stock 118,608 $60.12 $7,130,428.30
Disclosure

SEC source: 0001104659-21-098247 · tm2121736-11_4seq1.xml · nonDerivative · entry 1

Bentley Raymond B. · CIK 0001825229 · Director · Executive Vice President · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 19,109,540

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 June 11, 2021.

F2 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions on July 28, 2021 at prices ranging from $59.77 to $60.32. 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
June 15, 2021 Filed Jun 17, 2021 20:43 UTC BENTLEY SYSTEMS INC BSY · Entity 438 GrantClass B Common Stock 516 $0.00 $0.00
Disclosure

SEC source: 0001104659-21-082655 · tm2119958-3_4seq1.xml · nonDerivative · entry 1

Bentley Raymond B. · CIK 0001825229 · Director · Executive Vice President · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 19,228,148

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 24, 2021 Filed Mar 26, 2021 20:26 UTC BENTLEY SYSTEMS INC BSY · Entity 438 GrantClass B Common Stock 780 $0.00 $0.00
Disclosure

SEC source: 0001104659-21-042469 · tm2111006-7_4seq1.xml · nonDerivative · entry 1

Bentley Raymond B. · CIK 0001825229 · Director · Executive Vice President · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 19,227,632

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
January 21, 2021 Filed Jan 25, 2021 21:23 UTC BENTLEY SYSTEMS INC BSY · Entity 438 Tax withholdingClass B Common Stock 4,449 $44.23 $196,779.27
Disclosure

SEC source: 0001104659-21-007182 · tm214110-3_4seq1.xml · nonDerivative · entry 2

Bentley Raymond B. · CIK 0001825229 · Director · Executive Vice President · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 19,226,852

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
January 21, 2021 Filed Jan 25, 2021 21:23 UTC BENTLEY SYSTEMS INC BSY · Entity 438 GrantClass B Common Stock 14,965 $44.23 $661,901.95
Disclosure

SEC source: 0001104659-21-007182 · tm214110-3_4seq1.xml · nonDerivative · entry 1

Bentley Raymond B. · CIK 0001825229 · Director · Executive Vice President · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 19,231,301

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
December 22, 2020 Filed Dec 28, 2020 21:57 UTC BENTLEY SYSTEMS INC BSY · Entity 438 GrantClass B Common Stock 854 $0.00 $0.00
Disclosure

SEC source: 0001104659-20-139834 · tm2039300-7_4seq1.xml · nonDerivative · entry 3

Bentley Raymond B. · CIK 0001825229 · Director · Executive Vice President · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 19,216,336

F2 · 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 15, 2020 Filed Dec 28, 2020 21:57 UTC BENTLEY SYSTEMS INC BSY · Entity 438 GiftClass B Common Stock 560,278 $0.00 $0.00
Disclosure

SEC source: 0001104659-20-139834 · tm2039300-7_4seq1.xml · nonDerivative · entry 2

Bentley Raymond B. · CIK 0001825229 · Director · Executive Vice President · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 19,215,482

F1 · kind: Represents two separate and equal bona fide gifts of 280,139 shares of Class B Common Stock.

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December 15, 2020 Filed Dec 28, 2020 21:57 UTC BENTLEY SYSTEMS INC BSY · Entity 438 GiftClass B Common Stock 50,000 $0.00 $0.00
Disclosure

SEC source: 0001104659-20-139834 · tm2039300-7_4seq1.xml · nonDerivative · entry 1

Bentley Raymond B. · CIK 0001825229 · Director · Executive Vice President · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 19,775,760

Read SEC document
October 16, 2020 Filed Oct 20, 2020 21:04 UTC BENTLEY SYSTEMS INC BSY · Entity 438 Tax withholdingClass B Common Stock 296 $22.00 $6,512.00
Disclosure

SEC source: 0001104659-20-116476 · a4.xml · nonDerivative · entry 5

Bentley Raymond B. · CIK 0001825229 · Director · Executive Vice President · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 19,825,760

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
September 03, 2020 Filed Oct 20, 2020 21:04 UTC BENTLEY SYSTEMS INC BSY · Entity 438 GrantClass B Common Stock 1,952 $0.00 $0.00
Disclosure

SEC source: 0001104659-20-116476 · a4.xml · nonDerivative · entry 4

Bentley Raymond B. · CIK 0001825229 · Director · Executive Vice President · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 19,826,056

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 02, 2020 Filed Oct 20, 2020 21:04 UTC BENTLEY SYSTEMS INC BSY · Entity 438 GrantClass B Common Stock 97,604 $0.00 $0.00
Disclosure

SEC source: 0001104659-20-116476 · a4.xml · nonDerivative · entry 3

Bentley Raymond B. · CIK 0001825229 · Director · Executive Vice President · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 19,824,104

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
July 10, 2020 Filed Oct 20, 2020 21:04 UTC BENTLEY SYSTEMS INC BSY · Entity 438 GrantClass B Common Stock 680 $0.00 $0.00
Disclosure

SEC source: 0001104659-20-116476 · a4.xml · nonDerivative · entry 2

Bentley Raymond B. · CIK 0001825229 · Director · Executive Vice President · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 19,726,500

F2 · kind: Represents a grant of restricted stock that vested upon the consummation of the Issuer's initial public offering.

Read SEC document
June 12, 2020 Filed Oct 20, 2020 21:04 UTC BENTLEY SYSTEMS INC BSY · Entity 438 GrantClass B Common Stock 1,948 $0.00 $0.00
Disclosure

SEC source: 0001104659-20-116476 · a4.xml · nonDerivative · entry 1

Bentley Raymond B. · CIK 0001825229 · Director · Executive Vice President · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 19,725,820

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

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