BSY

SEC source: 0001104659-23-085387 · tm2321095-5_4seq1.xml · nonDerivative · entry 4

BENTLEY GREGORY S · CIK 0001214661 · Director · Chairman, CEO & President · 10% owner

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 7,939,535

F3 · kind: As previously disclosed by Bentley Systems, Incorporated (the "Company"), during the second quarter of 2022 the Company began to exercise its right to require that certain awardees of equity compensation and recipients of distributions from the Company's nonqualified deferred compensation plan receive vested awards and distributions (as applicable) in the form of gross quantities of Company Class B Common Stock (the "Common Stock") and to require such awardees and recipients to promptly reimburse the Company for their tax withholding amounts in cash. Prior to that election, all such vesting and distributions were made on a net basis, with the Company withholding shares of Common Stock in consideration of remitting withholding taxes on behalf of recipients.

F4 · kind: Due to a 1,000 character limit, Footnote 4 is a continuation of Footnote 3: Accordingly, in light of this change in practice, the Reporting Person entered into a 10b5-1 trading plan on August 12, 2022 (the "Plan") to sell previously-owned shares of Common Stock for the primary purpose of meeting his current and future tax withholding obligations. All sales reflected on this Form 4 were made pursuant to the Plan.

F6 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions on July 27, 2023 at prices ranging from $52.39 to $53.36. The Reporting Person undertakes to provide to the Company, any security holder of the Company, 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.

SEC source: 0001104659-23-085390 · tm2321095-6_4seq1.xml · nonDerivative · entry 3

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 17,340,432

F3 · kind: Represents shares withheld by the Issuer to cover taxes owed by the Reporting Person in respect of the Bonus Pool Payment.

SEC source: 0001104659-23-085390 · tm2321095-6_4seq1.xml · nonDerivative · entry 2

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 17,341,263

F2 · kind: Represents the stock portion of compensation paid to the Reporting Person pursuant to the Issuer's Bonus Pool Plan (the "Bonus Pool Payment").

SEC source: 0001104659-23-085390 · tm2321095-6_4seq1.xml · nonDerivative · entry 1

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 17,339,362

F1 · kind: Represents compensation paid to the Reporting Person and deferred into the Issuer's non-qualified deferred compensation plan and invested in fully-vested phantom shares that are distributable to the Reporting Person as shares of Class B Common Stock at a future date in accordance with the terms of the plan and the Reporting Person's plan election.

SEC source: 0001104659-23-085387 · tm2321095-5_4seq1.xml · nonDerivative · entry 3

BENTLEY GREGORY S · CIK 0001214661 · Director · Chairman, CEO & President · 10% owner

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 7,965,230

F3 · kind: As previously disclosed by Bentley Systems, Incorporated (the "Company"), during the second quarter of 2022 the Company began to exercise its right to require that certain awardees of equity compensation and recipients of distributions from the Company's nonqualified deferred compensation plan receive vested awards and distributions (as applicable) in the form of gross quantities of Company Class B Common Stock (the "Common Stock") and to require such awardees and recipients to promptly reimburse the Company for their tax withholding amounts in cash. Prior to that election, all such vesting and distributions were made on a net basis, with the Company withholding shares of Common Stock in consideration of remitting withholding taxes on behalf of recipients.

F4 · kind: Due to a 1,000 character limit, Footnote 4 is a continuation of Footnote 3: Accordingly, in light of this change in practice, the Reporting Person entered into a 10b5-1 trading plan on August 12, 2022 (the "Plan") to sell previously-owned shares of Common Stock for the primary purpose of meeting his current and future tax withholding obligations. All sales reflected on this Form 4 were made pursuant to the Plan.

F5 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions on July 26, 2023 at prices ranging from $52.62 to $53.52. The Reporting Person undertakes to provide to the Company, any security holder of the Company, 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.

SEC source: 0001104659-23-085387 · tm2321095-5_4seq1.xml · nonDerivative · entry 2

BENTLEY GREGORY S · CIK 0001214661 · Director · Chairman, CEO & President · 10% owner

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 8,006,831

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

SEC source: 0001104659-23-085387 · tm2321095-5_4seq1.xml · nonDerivative · entry 1

BENTLEY GREGORY S · CIK 0001214661 · Director · Chairman, CEO & President · 10% owner

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 8,032,940

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").

SEC source: 0001104659-23-084299 · tm2321095-4_4seq1.xml · nonDerivative · entry 3

BENTLEY GREGORY S · CIK 0001214661 · Director · Chairman, CEO & President · 10% owner

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 7,973,588

F1 · kind: As previously disclosed by Bentley Systems, Incorporated (the "Company"), during the second quarter of 2022 the Company began to exercise its right to require that certain awardees of equity compensation and recipients of distributions from the Company's nonqualified deferred compensation plan receive vested awards and distributions (as applicable) in the form of gross quantities of Company Class B Common Stock (the "Common Stock") and to require such awardees and recipients to promptly reimburse the Company for their tax withholding amounts in cash. Prior to that election, all such vesting and distributions were made on a net basis, with the Company withholding shares of Common Stock in consideration of remitting withholding taxes on behalf of recipients.

F2 · kind: Due to a 1,000 character limit, Footnote 2 is a continuation of Footnote 1: Accordingly, in light of this change in practice, the Reporting Person entered into a 10b5-1 trading plan on August 12, 2022 (the "Plan") to sell previously-owned shares of Common Stock for the primary purpose of meeting his current and future tax withholding obligations. All sales reflected on this Form 4 were made pursuant to the Plan.

F5 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions on July 25, 2023 at prices ranging from $53.89 to $54.00. The Reporting Person undertakes to provide to the Company, any security holder of the Company, 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.

SEC source: 0001104659-23-084299 · tm2321095-4_4seq1.xml · nonDerivative · entry 2

BENTLEY GREGORY S · CIK 0001214661 · Director · Chairman, CEO & President · 10% owner

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 7,978,727

F1 · kind: As previously disclosed by Bentley Systems, Incorporated (the "Company"), during the second quarter of 2022 the Company began to exercise its right to require that certain awardees of equity compensation and recipients of distributions from the Company's nonqualified deferred compensation plan receive vested awards and distributions (as applicable) in the form of gross quantities of Company Class B Common Stock (the "Common Stock") and to require such awardees and recipients to promptly reimburse the Company for their tax withholding amounts in cash. Prior to that election, all such vesting and distributions were made on a net basis, with the Company withholding shares of Common Stock in consideration of remitting withholding taxes on behalf of recipients.

F2 · kind: Due to a 1,000 character limit, Footnote 2 is a continuation of Footnote 1: Accordingly, in light of this change in practice, the Reporting Person entered into a 10b5-1 trading plan on August 12, 2022 (the "Plan") to sell previously-owned shares of Common Stock for the primary purpose of meeting his current and future tax withholding obligations. All sales reflected on this Form 4 were made pursuant to the Plan.

F4 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions on July 25, 2023 at prices ranging from $52.89 to $53.88. The Reporting Person undertakes to provide to the Company, any security holder of the Company, 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.

SEC source: 0001104659-23-084299 · tm2321095-4_4seq1.xml · nonDerivative · entry 1

BENTLEY GREGORY S · CIK 0001214661 · Director · Chairman, CEO & President · 10% owner

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 8,070,445

F1 · kind: As previously disclosed by Bentley Systems, Incorporated (the "Company"), during the second quarter of 2022 the Company began to exercise its right to require that certain awardees of equity compensation and recipients of distributions from the Company's nonqualified deferred compensation plan receive vested awards and distributions (as applicable) in the form of gross quantities of Company Class B Common Stock (the "Common Stock") and to require such awardees and recipients to promptly reimburse the Company for their tax withholding amounts in cash. Prior to that election, all such vesting and distributions were made on a net basis, with the Company withholding shares of Common Stock in consideration of remitting withholding taxes on behalf of recipients.

F2 · kind: Due to a 1,000 character limit, Footnote 2 is a continuation of Footnote 1: Accordingly, in light of this change in practice, the Reporting Person entered into a 10b5-1 trading plan on August 12, 2022 (the "Plan") to sell previously-owned shares of Common Stock for the primary purpose of meeting his current and future tax withholding obligations. All sales reflected on this Form 4 were made pursuant to the Plan.

F3 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions on July 24, 2023 at prices ranging from $52.81 to $53.66. The Reporting Person undertakes to provide to the Company, any security holder of the Company, 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.

SEC source: 0001104659-23-083843 · tm2321095-2_4seq1.xml · nonDerivative · entry 1

Andre Werner · CIK 0001825257 · Chief Financial Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 239,725

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.

SEC source: 0001104659-23-083846 · tm2321095-3_4seq1.xml · nonDerivative · entry 1

Ballard Brock · CIK 0001963448 · Chief Revenue Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 55,264

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.

SEC source: 0001104659-23-080328 · tm2321095-1_4seq1.xml · nonDerivative · entry 2

Shaman David R. · CIK 0001825193 · Chief Legal Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 624,622

F4 · 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.

SEC source: 0001104659-23-080328 · tm2321095-1_4seq1.xml · nonDerivative · entry 1

Shaman David R. · CIK 0001825193 · Chief Legal Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 626,248

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

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 June 30, 2023 for which the Reporting Person's enrollment and contribution elections were made in December 2022.

SEC source: 0001104659-23-073774 · tm2317958-11_4seq1.xml · nonDerivative · entry 1

Andre Werner · CIK 0001825257 · Chief Financial Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 241,030

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.

SEC source: 0001104659-23-073772 · tm2317958-10_4seq1.xml · nonDerivative · entry 1

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 17,186,599

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.

SEC source: 0001104659-23-073770 · tm2317958-9_4seq1.xml · nonDerivative · entry 1

Cumins Nicholas · CIK 0001896877 · Chief Operating Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 163,530

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.

SEC source: 0001104659-23-073768 · tm2317958-8_4seq1.xml · nonDerivative · entry 1

Campbell Michael M · CIK 0001963451 · Chief Product Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 98,373

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.

SEC source: 0001104659-23-073767 · tm2317958-7_4seq1.xml · nonDerivative · entry 1

Griswold Kirk B. · CIK 0001825243 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 443,549

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.

SEC source: 0001104659-23-073764 · tm2317958-6_4seq1.xml · nonDerivative · entry 1

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 17,338,889

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.

SEC source: 0001104659-23-073763 · tm2317958-5_4seq1.xml · nonDerivative · entry 1

BENTLEY GREGORY S · CIK 0001214661 · Director · Chairman, CEO & President · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 8,128,141

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.

SEC source: 0001104659-23-073759 · tm2317958-4_4seq1.xml · nonDerivative · entry 1

Shaman David R. · CIK 0001825193 · Chief Legal Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 628,502

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.

SEC source: 0001104659-23-073758 · tm2317958-3_4seq1.xml · nonDerivative · entry 1

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 12,295,703

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.

SEC source: 0001104659-23-073753 · tm2317958-2_4seq1.xml · nonDerivative · entry 1

Ballard Brock · CIK 0001963448 · Chief Revenue Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 55,775

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.

SEC source: 0001104659-23-068894 · tm2317958-1_4seq1.xml · nonDerivative · entry 1

Griswold Kirk B. · CIK 0001825243 · Director

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 443,483

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 15, 2022.

F2 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions on June 5, 2023 at prices ranging from $49.60 to $50.34. 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.

SEC source: 0001104659-23-066027 · tm2314780-8_4seq1.xml · nonDerivative · entry 1

Hughes Brian F. · CIK 0001825326 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 25,757

F1 · kind: Represents director compensation paid to Mr. Hughes pursuant to the Issuer's Non-Employee Director Compensation Policy upon his reelection to the Issuer's Board of Directors.

SEC source: 0001104659-23-066024 · tm2314780-9_4seq1.xml · nonDerivative · entry 1

HAUGEN JANET BRUTSCHEA · CIK 0001185136 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 20,455

F1 · kind: Represents director compensation paid to Ms. Haugen pursuant to the Issuer's Non-Employee Director Compensation Policy upon her reelection to the Issuer's Board of Directors.

SEC source: 0001104659-23-066020 · tm2314780-10_4seq1.xml · nonDerivative · entry 1

Griswold Kirk B. · CIK 0001825243 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 480,230

F1 · kind: Represents director compensation paid to Mr. Griswold pursuant to the Issuer's Non-Employee Director Compensation Policy upon his reelection to the Issuer's Board of Directors.

SEC source: 0001104659-23-064121 · tm2314780-7_4seq1.xml · derivative · entry 6

Andre Werner · CIK 0001825257 · Chief Financial Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 19,226

Underlying: Class B Common Stock · 15,774 shares

Expires 2024-03-21

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F2 · derivative.exercise_date: These options are fully vested and exercisable.

SEC source: 0001104659-23-064121 · tm2314780-7_4seq1.xml · derivative · entry 5

Andre Werner · CIK 0001825257 · Chief Financial Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Class B Common Stock · 21,875 shares

Expires 2023-05-28

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F2 · derivative.exercise_date: These options are fully vested and exercisable.

SEC source: 0001104659-23-064121 · tm2314780-7_4seq1.xml · nonDerivative · entry 4

Andre Werner · CIK 0001825257 · Chief Financial Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 240,983

F1 · kind: Represents the number of shares of Class B Common Stock owned by the Reporting Person and relinquished to the Issuer to cover the exercise price of options exercised via a stock swap exercise method.

SEC source: 0001104659-23-064121 · tm2314780-7_4seq1.xml · nonDerivative · entry 3

Andre Werner · CIK 0001825257 · Chief Financial Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 242,914

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

SEC source: 0001104659-23-064121 · tm2314780-7_4seq1.xml · nonDerivative · entry 2

Andre Werner · CIK 0001825257 · Chief Financial Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 227,140

F1 · kind: Represents the number of shares of Class B Common Stock owned by the Reporting Person and relinquished to the Issuer to cover the exercise price of options exercised via a stock swap exercise method.

SEC source: 0001104659-23-064121 · tm2314780-7_4seq1.xml · nonDerivative · entry 1

Andre Werner · CIK 0001825257 · Chief Financial Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 229,615

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

SEC source: 0001104659-23-063625 · tm2314780-6_4seq1.xml · nonDerivative · entry 1

Cumins Nicholas · CIK 0001896877 · Chief Operating Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 163,417

F1 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions on May 19, 2023 at prices ranging from $46.00 to $46.11. The Reporting Person undertakes to provide to the Company, any security holder of the Company, 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.

SEC source: 0001104659-23-063147 · tm2314780-5_4seq1.xml · derivative · entry 8

Shaman David R. · CIK 0001825193 · Chief Legal Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Class B Common Stock · 18,850 shares

Expires 2023-05-28

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F3 · derivative.exercise_date: These options were fully vested, and, following the exercises on May 18, 2023, have been exercised in full.

SEC source: 0001104659-23-063147 · tm2314780-5_4seq1.xml · derivative · entry 7

Shaman David R. · CIK 0001825193 · Chief Legal Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 18,850

Underlying: Class B Common Stock · 85,150 shares

Expires 2023-05-28

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F3 · derivative.exercise_date: These options were fully vested, and, following the exercises on May 18, 2023, have been exercised in full.

SEC source: 0001104659-23-063147 · tm2314780-5_4seq1.xml · nonDerivative · entry 4

Shaman David R. · CIK 0001825193 · Chief Legal Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 628,121

F2 · kind: Represents the number of shares of Class B Common Stock owned by the Reporting Person and relinquished to the Issuer to cover the exercise price of options exercised via a stock swap exercise method.

SEC source: 0001104659-23-063147 · tm2314780-5_4seq1.xml · nonDerivative · entry 3

Shaman David R. · CIK 0001825193 · Chief Legal Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 630,268

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

SEC source: 0001104659-23-063147 · tm2314780-5_4seq1.xml · nonDerivative · entry 2

Shaman David R. · CIK 0001825193 · Chief Legal Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 611,418

F1 · kind: Represents shares withheld by the Issuer to cover the exercise price and taxes in connection with a cashless exercise of stock options by the Reporting Person.

SEC source: 0001104659-23-063147 · tm2314780-5_4seq1.xml · nonDerivative · entry 1

Shaman David R. · CIK 0001825193 · Chief Legal Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 653,949

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

SEC source: 0001104659-23-062279 · tm2314780-4_4seq1.xml · derivative · entry 3

Andre Werner · CIK 0001825257 · Chief Financial Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 21,875

Underlying: Class B Common Stock · 11,875 shares

Expires 2023-05-28

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F2 · derivative.exercise_date: These options are fully vested.

SEC source: 0001104659-23-062279 · tm2314780-4_4seq1.xml · nonDerivative · entry 2

Andre Werner · CIK 0001825257 · Chief Financial Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 207,740

F1 · kind: Represents shares withheld by the Issuer to cover the exercise price and taxes in connection with a cashless exercise of stock options by the Reporting Person.

SEC source: 0001104659-23-062279 · tm2314780-4_4seq1.xml · nonDerivative · entry 1

Andre Werner · CIK 0001825257 · Chief Financial Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 213,245

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

SEC source: 0001104659-23-059769 · tm2314780-3_4seq1.xml · nonDerivative · entry 2

BENTLEY GREGORY S · CIK 0001214661 · Director · Chairman, CEO & President · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 8,125,905

SEC source: 0001104659-23-059769 · tm2314780-3_4seq1.xml · nonDerivative · entry 1

BENTLEY GREGORY S · CIK 0001214661 · Director · Chairman, CEO & President · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 8,136,962

F1 · kind: Represents a private sale of Class B Common Stock to a family trust in satisfaction of a prior obligation.

SEC source: 0001104659-23-059143 · tm2314780-2_4seq1.xml · nonDerivative · entry 1

Shaman David R. · CIK 0001825193 · Chief Legal Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 568,799

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 16, 2022.

F2 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions on May 9, 2023 at prices ranging from $45.00 to $45.17. 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.

SEC source: 0001104659-23-056567 · tm2314780-1_4seq1.xml · nonDerivative · entry 1

Shaman David R. · CIK 0001825193 · Chief Legal Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 575,253

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.

SEC source: 0001104659-23-054392 · tm2314141-2_4seq1.xml · nonDerivative · entry 3

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 17,335,884

F3 · kind: Represents shares withheld by the Issuer to cover taxes owed by the Reporting Person in respect of the Bonus Pool Payment.

SEC source: 0001104659-23-054392 · tm2314141-2_4seq1.xml · nonDerivative · entry 2

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 17,337,276

F2 · kind: Represents the stock portion of compensation paid to the Reporting Person pursuant to the Issuer's Bonus Pool Plan (the "Bonus Pool Payment").