[144] Bentley Systems, Incorporated SEC Filing

Rhea-AI Filing Summary

Bentley Systems (BSY) submitted a Form 144 proposing the sale of 300 shares of Class B common stock through Charles Schwab, with an aggregate market value of $16,069.50, scheduled approximately for 08/18/2025. The 300 shares were acquired as a gift from Keith Bentley on 10/15/2015. The filing lists multiple related sales during the past three months, including a sale of 150,000 shares on 07/07/2025 for $8,326,003.40 and sizable distributions on 08/13/2025 and 08/14/2025 producing proceeds in the hundreds of thousands to millions of dollars for various gift trusts. The filer represents no undisclosed material adverse information and certifies compliance with applicable trading rules.

Insights

Securities Analyst

TL;DR: Routine Rule 144 notice; small proposed sale but recent large related insider distributions are notable.

The Form 144 itself covers a modest proposed sale of 300 Class B shares valued at $16,069.50 to be executed via Charles Schwab on or about 08/18/2025. Material context comes from the disclosed prior transfers and sales: a 150,000-share disposition on 07/07/2025 generating $8,326,003.40 and multiple large trust sales on 08/13–08/14/2025 producing proceeds in the high six-figures to low seven-figures. From a market-structure perspective, the filing is a routine compliance disclosure but the recent pattern of sizable trust distributions and sales may affect free-float and short-term supply dynamics depending on total company float. No financial performance or forward guidance data is present in this filing.

Corporate Governance Expert

TL;DR: Disclosure aligns with Rule 144; multiple trust-related transfers and large sales warrant governance attention.

The notice documents a gift-based acquisition and subsequent planned sale under Rule 144, which is standard for insiders and related trusts. However, the record of numerous sales by various Keith A. Bentley trusts and the primary beneficial owner producing multi-million-dollar proceeds over recent months suggests a meaningful change in insider-held circulating shares. Governance teams should note the transfer history is clearly disclosed here, but this filing does not explain the rationale for the distributions or whether they reflect estate planning, diversification, or other motives. The filing does include the required representation that there is no undisclosed material adverse information.

Form 144 Filer Information	UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 144 NOTICE OF PROPOSED SALE OF SECURITIES PURSUANT TO RULE 144 UNDER THE SECURITIES ACT OF 1933
FORM 144

144: Filer Information

Filer CIK
Filer CCC
Is this a LIVE or TEST Filing?	LIVE TEST
Submission Contact Information
Name
Phone
E-Mail Address

144: Issuer Information

Name of Issuer

SEC File Number

Address of Issuer

Phone

Name of Person for Whose Account the Securities are To Be Sold

See the definition of "person" in paragraph (a) of Rule 144. Information is to be given not only as to the person for whose account the securities are to be sold but also as to all other persons included in that definition. In addition, information shall be given as to sales by all persons whose sales are required by paragraph (e) of Rule 144 to be aggregated with sales for the account of the person filing this notice.

Relationship to Issuer

144: Securities Information

Title of the Class of Securities To Be Sold	Name and Address of the Broker	Number of Shares or Other Units To Be Sold	Aggregate Market Value	Number of Shares or Other Units Outstanding	Approximate Date of Sale	Name the Securities Exchange
Class B Common Stock	Charles Schwab & Co 3000 Schwab Way Westlake TX 76262	300	16069.50	292093306	08/18/2025	Nasdaq

Furnish the following information with respect to the acquisition of the securities to be sold and with respect to the payment of all or any part of the purchase price or other consideration therefor:

144: Securities To Be Sold

Title of the Class	Date you Acquired	Nature of Acquisition Transaction	Name of Person from Whom Acquired	Is this a Gift?	Date Donor Acquired	Amount of Securities Acquired	Date of Payment	Nature of Payment *
Class B Common Stock	10/15/2015	Gift	Keith Bentley		08/14/1987	300	10/15/2015	Gift

* If the securities were purchased and full payment therefor was not made in cash at the time of purchase, explain in the table or in a note thereto the nature of the consideration given. If the consideration consisted of any note or other obligation, or if payment was made in installments describe the arrangement and state when the note or other obligation was discharged in full or the last installment paid.

Furnish the following information as to all securities of the issuer sold during the past 3 months by the person for whose account the securities are to be sold.

144: Securities Sold During The Past 3 Months

Name and Address of Seller	Title of Securities Sold	Date of Sale	Amount of Securities Sold	Gross Proceeds
Keith A. Bentley 2012 Gift Trust FBO Charlene 685 STOCKTON DRIVE Exton PA 19341	Class B Common Stock	08/14/2025	1427	73600.28
Keith A. Bentley 2012 Gift Trust FBO Jennifer 685 STOCKTON DRIVE Exton PA 19341	Class B Common Stock	08/14/2025	2568	184026.50
Keith A. Bentley 2012 Gift Trust FBO Robert 685 STOCKTON DRIVE Exton PA 19341	Class B Common Stock	08/14/2025	1427	73600.28
Keith A. Bentley 2012 Gift Trust FBO Charlene 685 STOCKTON DRIVE Exton PA 19341	Class B Common Stock	08/13/2025	17778	926108.18
Keith A. Bentley 2012 Gift Trust FBO Jennifer 685 STOCKTON DRIVE Exton PA 19341	Class B Common Stock	08/13/2025	44444	2315218.36
Keith A. Bentley 2012 Gift Trust FBO Robert 685 STOCKTON DRIVE Exton PA 19341	Class B Common Stock	08/13/2025	17778	926108.18
Keith A. Bentley 685 STOCKTON DRIVE Exton PA 19341	Class B Common Stock	07/07/2025	150000	8326003.40
Keith A. Bentley 2007 Gift Trust FBO David 685 STOCKTON DRIVE Exton PA 19341	Class B Common Stock	05/28/2025	3	144.06
Keith A. Bentley 2007 Gift Trust FBO David 685 STOCKTON DRIVE Exton PA 19341	Class B Common Stock	05/27/2025	20741	999876.81
Keith A. Bentley 2012 Gift Trust FBO Charlene 685 STOCKTON DRIVE Exton PA 19341	Class B Common Stock	05/23/2025	73	3463.63
Keith A. Bentley 2012 Gift Trust FBO Charlene 685 STOCKTON DRIVE Exton PA 19341	Class B Common Stock	05/22/2025	4316	205544.46
Keith A. Bentley 2012 Gift Trust FBO Charlene 685 STOCKTON DRIVE Exton PA 19341	Class B Common Stock	05/21/2025	854	41010.82

144: Remarks and Signature

Remarks

Date of Notice

ATTENTION:

The person for whose account the securities to which this notice relates are to be sold hereby represents by signing this notice that he does not know any material adverse information in regard to the current and prospective operations of the Issuer of the securities to be sold which has not been publicly disclosed. If such person has adopted a written trading plan or given trading instructions to satisfy Rule 10b5-1 under the Exchange Act, by signing the form and indicating the date that the plan was adopted or the instruction given, that person makes such representation as of the plan adoption or instruction date.

Signature

ATTENTION: Intentional misstatements or omission of facts constitute Federal Criminal Violations (See 18 U.S.C. 1001)