BSY

SEC source: 0001104659-23-054392 · tm2314141-2_4seq1.xml · nonDerivative · entry 1

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 17,334,095

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: 0001104659-23-054385 · tm2314141-1_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: 8,266,653

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: 0001104659-23-054385 · tm2314141-1_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: 8,310,325

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: 0001104659-23-050367 · tm2313339-5_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: 8,211,049

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.

SEC source: 0001104659-23-050367 · tm2313339-5_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: 8,211,289

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 April 25, 2023 at prices ranging from $40.98 to $41.94. 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: 0001104659-23-050367 · tm2313339-5_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: 8,228,960

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.

SEC source: 0001104659-23-050367 · tm2313339-5_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: 8,229,060

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 April 24, 2023 at prices ranging from $41.85 to $42.77. 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: 0001104659-23-048403 · tm2313339-4_4seq1.xml · nonDerivative · entry 1

Cumins Nicholas · CIK 0001896877 · Chief Operating Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 191,417

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: 0001104659-23-048401 · tm2313339-3_4seq.xml · nonDerivative · entry 1

Shaman David R. · CIK 0001825193 · Chief Legal Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 585,727

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: 0001104659-23-048397 · tm2313339-2_4seq.xml · nonDerivative · entry 1

Ballard Brock · CIK 0001963448 · Chief Revenue Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 55,731

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: 0001104659-23-048394 · tm2313339-1_4seq.xml · nonDerivative · entry 1

Andre Werner · CIK 0001825257 · Chief Financial Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 201,370

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: 0001104659-23-042233 · tm2311346-3_4seq1.xml · nonDerivative · entry 1

Shaman David R. · CIK 0001825193 · Chief Legal Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 586,573

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: 0001104659-23-042231 · tm2311346-2_4seq1.xml · nonDerivative · entry 1

Griswold Kirk B. · CIK 0001825243 · Director

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 476,017

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 April 3, 2023 at prices ranging from $42.49 to $43.32. 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.

SEC source: 0001104659-23-040931 · tm2311346-1_4seq1.xml · nonDerivative · entry 2

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

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 12,295,497

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 August 10, 2022.

F3 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions on March 31, 2023 at prices ranging from $42.50 to $42.99. 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: 0001104659-23-040931 · tm2311346-1_4seq1.xml · nonDerivative · entry 1

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

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 12,594,258

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 August 10, 2022.

F2 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions on March 30, 2023 at prices ranging from $42.50 to $42.575. 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: 0001104659-23-035083 · tm2310046-5_4seq1.xml · derivative · entry 3

Griswold Kirk B. · CIK 0001825243 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Class B Common Stock · 10,000 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 were fully vested and have been exercised in full.

SEC source: 0001104659-23-035083 · tm2310046-5_4seq1.xml · nonDerivative · entry 2

Griswold Kirk B. · CIK 0001825243 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 511,017

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

SEC source: 0001104659-23-035083 · tm2310046-5_4seq1.xml · nonDerivative · entry 1

Griswold Kirk B. · CIK 0001825243 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 512,306

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: 0001104659-23-035082 · tm2310046-4_4seq1.xml · nonDerivative · entry 1

Shaman David R. · CIK 0001825193 · Chief Legal Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 590,423

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: 0001104659-23-035081 · tm2310046-3_4seq1.xml · nonDerivative · entry 1

Ballard Brock · CIK 0001963448 · Chief Revenue Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 55,909

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: 0001104659-23-035080 · tm2310046-2_4seq1.xml · nonDerivative · entry 1

Cumins Nicholas · CIK 0001896877 · Chief Operating Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 192,992

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: 0001104659-23-035075 · tm2310046-1_4seq1.xml · nonDerivative · entry 1

Andre Werner · CIK 0001825257 · Chief Financial Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 201,643

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: 0001104659-23-033924 · tm238296-19_4seq1.xml · nonDerivative · entry 1

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

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 8,274,683

SEC source: 0001104659-23-032851 · tm238296-18_4seq1.xml · nonDerivative · entry 1

Andre Werner · CIK 0001825257 · Chief Financial Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 202,614

F1 · kind: Represents a time-based restricted stock 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.

SEC source: 0001104659-23-032848 · tm238296-17_4seq1.xml · nonDerivative · entry 1

Cumins Nicholas · CIK 0001896877 · Chief Operating Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 195,880

F1 · kind: Represents a time-based restricted stock 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.

SEC source: 0001104659-23-032843 · tm238296-16_4seq1.xml · nonDerivative · entry 1

Campbell Michael M · CIK 0001963451 · Chief Product Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 98,285

F1 · kind: Represents a time-based restricted stock 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.

SEC source: 0001104659-23-032842 · tm238296-15_4seq1.xml · nonDerivative · entry 1

Shaman David R. · CIK 0001825193 · Chief Legal Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 716,579

F1 · kind: Represents a time-based restricted stock 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.

SEC source: 0001104659-23-032841 · tm238296-14_4seq.xml · nonDerivative · entry 1

Ballard Brock · CIK 0001963448 · Chief Revenue Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 56,141

F1 · kind: Represents a time-based restricted stock 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.

SEC source: 0001104659-23-030638 · tm238296-13_4seq1.xml · nonDerivative · entry 1

Andre Werner · CIK 0001825257 · Chief Financial Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 187,697

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: 0001104659-23-030634 · tm238296-12_4seq1.xml · nonDerivative · entry 1

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

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 17,185,547

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: 0001104659-23-030630 · tm238296-11_4seq1.xml · nonDerivative · entry 1

Cumins Nicholas · CIK 0001896877 · Chief Operating Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 176,413

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: 0001104659-23-030628 · tm238296-10_4seq1.xml · nonDerivative · entry 1

Campbell Michael M · CIK 0001963451 · Chief Product Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 82,112

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: 0001104659-23-030624 · tm238296-9_4seq1.xml · nonDerivative · entry 1

Griswold Kirk B. · CIK 0001825243 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 502,306

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: 0001104659-23-030619 · tm238296-8_4seq1.xml · nonDerivative · entry 1

Bentley Keith A. · CIK 0001825187 · Director · Chief Technology Officer · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 17,333,305

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: 0001104659-23-030615 · tm238296-7_4seq1.xml · nonDerivative · entry 1

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

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 8,287,277

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: 0001104659-23-030613 · tm238296-6_4seq1.xml · nonDerivative · entry 1

Shaman David R. · CIK 0001825193 · Chief Legal Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 702,447

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: 0001104659-23-030610 · tm238296-5_4seq1.xml · nonDerivative · entry 1

Hollister David J. · CIK 0001825456 · Chief Investment Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 1,964,392

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: 0001104659-23-030606 · tm238296-4_4seq1.xml · nonDerivative · entry 1

Ballard Brock · CIK 0001963448 · Chief Revenue Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 45,150

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.

SEC source: 0001104659-23-030604 · tm238296-3_4seq1.xml · nonDerivative · entry 1

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

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 12,645,088

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: 0001104659-23-029629 · tm238296-2_4seq1.xml · nonDerivative · entry 2

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

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 12,644,816

F1 · kind: The sales reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan.

F3 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions on March 6, 2023 at prices ranging from $42.50 to $42.525. 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: 0001104659-23-029629 · tm238296-2_4seq1.xml · nonDerivative · entry 1

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

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 12,653,172

F1 · kind: The sales reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan.

F2 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions on March 3, 2023 at prices ranging from $42.50 to $42.57. 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: 0001104659-23-027974 · tm238296-1_4seq1.xml · nonDerivative · entry 1

Shaman David R. · CIK 0001825193 · Chief Legal Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 701,902

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: 0001104659-23-011207 · tm235463-2_4seq1.xml · nonDerivative · entry 1

Shaman David R. · CIK 0001825193 · Chief Legal Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 703,820

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.

SEC source: 0001104659-23-011196 · tm235463-1_4seq1.xml · nonDerivative · entry 1

Hollister David J. · CIK 0001825456 · Chief Investment Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 1,961,948

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 15, 2022.

F2 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions on February 2, 2023 at prices ranging from $41.00 to $41.48. 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: 0001104659-23-007041 · tm231633-11_4seq1.xml · nonDerivative · entry 4

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

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 8,284,318

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 (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 January 25, 2023 at prices ranging from $36.59 to $37.39. 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: 0001104659-23-007046 · tm231633-16_4seq1.xml · nonDerivative · entry 2

Andre Werner · CIK 0001825257 · Chief Financial Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 187,648

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.

SEC source: 0001104659-23-007046 · tm231633-16_4seq1.xml · nonDerivative · entry 1

Andre Werner · CIK 0001825257 · Chief Financial Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 192,040

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

SEC source: 0001104659-23-007045 · tm231633-15_4seq1.xml · nonDerivative · entry 2

Cumins Nicholas · CIK 0001896877 · Chief Operating Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 176,277

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.

SEC source: 0001104659-23-007045 · tm231633-15_4seq1.xml · nonDerivative · entry 1

Cumins Nicholas · CIK 0001896877 · Chief Operating Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 188,242

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

SEC source: 0001104659-23-007044 · tm231633-14_4seq1.xml · nonDerivative · entry 2

Campbell Michael M · CIK 0001963451 · Chief Product Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 82,016

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.