Gregory S. Bentley

CIK: 0001214661

Transaction Breakdown

Open Market Buys (P)0 (0.0%)

High conviction signal

Open Market Sales (S)3 (6.8%)

Position reduction

Option Exercises (M)0 (0.0%)

Derivative conversions

Awards (A)18 (40.9%)

Compensation grants

Other (G, F, J, C, D, …)23 (52.3%)

Gifts, tax withholding, conversions, dispositions to the issuer and other codes

Companies & Roles (1)

BSY

BENTLEY SYSTEMS INC

DirectorOfficer10% Owner

Discretionary Trading P&L

Holdings

Transaction History (44 total)

BSY
BENTLEY SYSTEMS INC
Oct 22, 2026
Tax Payment(F)
Direct
27.9K shares at avg. $39.41$1.1M
BSY
BENTLEY SYSTEMS INC
Oct 22, 2026
Award(A)
Direct
63.8K shares at avg. $39.41$2.5M
BSY
BENTLEY SYSTEMS INC
Sep 29, 2026
Award(A)
Direct
3.7K shares-
BSY
BENTLEY SYSTEMS INC
Aug 12, 2026
Gift(G)
Direct
703 shares-
BSY
BENTLEY SYSTEMS INC
Aug 12, 2026
Gift(G)
Direct
281 shares-
BSY
BENTLEY SYSTEMS INC
Jul 23, 2026
Award(A)
Direct
61K shares at avg. $30.12$1.8M
BSY
BENTLEY SYSTEMS INC
Jul 23, 2026
Tax Payment(F)
Direct
26.7K shares at avg. $30.12$804K
BSY
BENTLEY SYSTEMS INC
Jun 11, 2026
Award(A)
Direct
3.7K shares-
BSY
BENTLEY SYSTEMS INC
Apr 23, 2026
Tax Payment(F)
Direct
27.1K shares at avg. $32.65$886K
BSY
BENTLEY SYSTEMS INC
Apr 23, 2026
Award(A)
Direct
62K shares at avg. $32.65$2.0M
BSY
BENTLEY SYSTEMS INC
Mar 19, 2026
Award(A)
Direct
3K shares-
BSY
BENTLEY SYSTEMS INC
Mar 10, 2026
Sale(S)
Direct
100 shares at avg. $40.01$4K
BSY
BENTLEY SYSTEMS INC
Mar 3, 2026
Gift(G)
Direct
672 shares-
BSY
BENTLEY SYSTEMS INC
Mar 3, 2026
Gift(G)
Direct
672 shares-
BSY
BENTLEY SYSTEMS INC
Jan 23, 2026
Award(A)
Direct
36.8K shares at avg. $38.84$1.4M
BSY
BENTLEY SYSTEMS INC
Jan 23, 2026
Tax Payment(F)
Direct
16.1K shares at avg. $38.84$625K
BSY
BENTLEY SYSTEMS INC
Dec 11, 2025
Award(A)
Direct
4K shares-
BSY
BENTLEY SYSTEMS INC
Dec 1, 2025
Tax Payment(F)
Direct
8.9K shares at avg. $41.85$374K
BSY
BENTLEY SYSTEMS INC
Oct 22, 2025
Tax Payment(F)
Direct
13.2K shares at avg. $52.01$686K
BSY
BENTLEY SYSTEMS INC
Oct 22, 2025
Award(A)
Direct
30.1K shares at avg. $52.01$1.6M
BSY
BENTLEY SYSTEMS INC
Sep 30, 2025
Award(A)
Direct
3.2K shares-
BSY
BENTLEY SYSTEMS INC
Sep 2, 2025
Sale(S)
Direct
37.2K shares at avg. $54.83$2.0M
BSY
BENTLEY SYSTEMS INC
Aug 27, 2025
Gift(G)
Direct
351 shares-
BSY
BENTLEY SYSTEMS INC
Aug 21, 2025
Gift(G)
Direct
9.3K shares-
BSY
BENTLEY SYSTEMS INC
Jul 24, 2025
Tax Payment(F)
Direct
13.4K shares at avg. $58.35$785K

		Type	Shares	Price		Ownership
Oct 22, 2026	BSY BENTLEY SYSTEMS INC	Tax Payment(F)	27,903	$39.41	$1,099,657	Direct
Oct 22, 2026	BSY BENTLEY SYSTEMS INC	Award(A)	63,793	$39.41	$2,514,082	Direct
Sep 29, 2026	BSY BENTLEY SYSTEMS INC	Award(A)	3,691	-	$0	Direct
Aug 12, 2026	BSY BENTLEY SYSTEMS INC	Gift(G)	703	-	$0	Direct
Aug 12, 2026	BSY BENTLEY SYSTEMS INC	Gift(G)	281	-	$0	Direct
Jul 23, 2026	BSY BENTLEY SYSTEMS INC	Award(A)	61,037	$30.12	$1,838,434	Direct
Jul 23, 2026	BSY BENTLEY SYSTEMS INC	Tax Payment(F)	26,698	$30.12	$804,144	Direct
Jun 11, 2026	BSY BENTLEY SYSTEMS INC	Award(A)	3,749	-	$0	Direct
Apr 23, 2026	BSY BENTLEY SYSTEMS INC	Tax Payment(F)	27,133	$32.65	$885,892	Direct
Apr 23, 2026	BSY BENTLEY SYSTEMS INC	Award(A)	62,032	$32.65	$2,025,345	Direct
Mar 19, 2026	BSY BENTLEY SYSTEMS INC	Award(A)	3,019	-	$0	Direct
Mar 10, 2026	BSY BENTLEY SYSTEMS INC	Sale(S)	100	$40.01	$4,001	Direct
Mar 3, 2026	BSY BENTLEY SYSTEMS INC	Gift(G)	672	-	$0	Direct
Mar 3, 2026	BSY BENTLEY SYSTEMS INC	Gift(G)	672	-	$0	Direct
Jan 23, 2026	BSY BENTLEY SYSTEMS INC	Award(A)	36,765	$38.84	$1,427,953	Direct
Jan 23, 2026	BSY BENTLEY SYSTEMS INC	Tax Payment(F)	16,081	$38.84	$624,586	Direct
Dec 11, 2025	BSY BENTLEY SYSTEMS INC	Award(A)	3,958	-	-	Direct
Dec 1, 2025	BSY BENTLEY SYSTEMS INC	Tax Payment(F)	8,932	$41.85	$373,804	Direct
Oct 22, 2025	BSY BENTLEY SYSTEMS INC	Tax Payment(F)	13,181	$52.01	$685,544	Direct
Oct 22, 2025	BSY BENTLEY SYSTEMS INC	Award(A)	30,135	$52.01	$1,567,321	Direct
Sep 30, 2025	BSY BENTLEY SYSTEMS INC	Award(A)	3,185	-	-	Direct
Sep 2, 2025	BSY BENTLEY SYSTEMS INC	Sale(S)	37,160	$54.83	$2,037,576	Direct
Aug 27, 2025	BSY BENTLEY SYSTEMS INC	Gift(G)	351	-	-	Direct
Aug 21, 2025	BSY BENTLEY SYSTEMS INC	Gift(G)	9,349	-	-	Direct
Jul 24, 2025	BSY BENTLEY SYSTEMS INC	Tax Payment(F)	13,445	$58.35	$784,516	Direct

1-25 of 44 transactions

About BENTLEY GREGORY S

BENTLEY GREGORY S (SEC CIK 0001214661) files insider reports with the SEC as Executive Chair & President of BENTLEY SYSTEMS INC (BSY).

Signal8 holds 29 ownership filings by BENTLEY GREGORY S, all Form 4s, filed between Sep 30, 2024 and Oct 26, 2026. Those filings report 44 transactions, from Sep 26, 2024 to Oct 22, 2026. Signal8's Form 4 history starts in Sep 2024.

The business address on BENTLEY GREGORY S's filings is in EXTON, PA.

Recent filings by BENTLEY GREGORY S

Oct 22, 2026: Tax withholding of BSY shares (Form 4, code F).
Oct 22, 2026: Grant or award of BSY shares (Form 4, code A).
Sep 29, 2026: Grant or award of BSY shares (Form 4, code A).
Aug 12, 2026: Gifts of BSY shares (2 lines, Form 4, code G).
Jul 23, 2026: Grant or award of BSY shares (Form 4, code A).

Other insiders filing for BENTLEY SYSTEMS INC (BSY)

Trimback Thomas F, Chief Accounting Officer
Bentley Raymond B., Director
Andre Werner, Chief Financial Officer
Rahden Andrew, Chief Revenue Officer
Cumins Nicholas, Chief Executive Officer
Moutte Julien, Chief Technology Officer

How to read Form 4 transaction codes