Director-linked trust may sell $11M Bentley Systems (NASDAQ: BSY) stock

Rhea-AI Filing Summary

BENTLEY SYSTEMS INC (BSY) received a Form 144 notice that the Bentley 2012 Generation Skipping Trust, for which a director is associated, may sell up to 300,000 shares of Class B stock through Charles Schwab & Co. The shares have an indicated aggregate market value of $11,082,000 and relate to a class with 290,577,762 shares outstanding, listed on Nasdaq. The shares were originally acquired as a gift on December 21, 2012, from Raymond B. Bentley.

Key Figures

Class B shares to be sold: 300,000 shares Aggregate market value: $11,082,000 Shares outstanding (Class B): 290,577,762 shares +3 more

6 metrics

Class B shares to be sold 300,000 shares Maximum number of BENTLEY SYSTEMS INC Class B shares covered by the Form 144

Aggregate market value $11,082,000 Value associated with 300,000 Class B shares to be sold

Shares outstanding (Class B) 290,577,762 shares Shares outstanding for the class related to the planned sale

Planned sale date 08/27/2026 Date listed in connection with the potential sale on Nasdaq

Acquisition date of shares 12/21/2012 Date the shares were acquired as a gift from Raymond B. Bentley

Seller account Bentley 2012 Generation Skipping Trust Trust for whose account the securities are to be sold

Key Terms

Rule 144, Generation Skipping Trust, Form 144, aggregate market value

4 terms

Rule 144 regulatory

"See the definition of "person" in paragraph (a) of Rule 144."

Rule 144 is a U.S. securities regulation that sets conditions under which restricted or insider-held shares can be legally resold to the public, such as required holding periods, availability of public information, limits on how much can be sold at once, and certain filing requirements. For investors it matters because it determines when previously locked-up shares can enter the market — like a release valve that can increase supply, affect share price, and signal insider intent.

Generation Skipping Trust financial

"Name of Person for Whose Account the Securities are To Be Sold | Bentley 2012 Generation Skipping Trust"

Form 144 regulatory

"144: Filer Information"

Form 144 is a document that investors must file with the government when they plan to sell a large number of shares of a company's stock. It helps ensure transparency so everyone knows how many shares are being sold and when, which can impact the stock's price.

aggregate market value financial

"class b | Charles Schwab & Co ... | 300000 | 11082000.00 | 290577762"

Aggregate market value is the combined price you would pay to buy all outstanding shares of a company or all companies in a group at current market prices — essentially the sum of each stock’s market capitalization. It matters to investors because it shows the overall size and weight of an investment or sector (like the total cost to buy every piece of a puzzle), helps compare scale across companies or markets, and influences index composition and risk exposure.

FAQ

What does the Form 144 filing for BSY disclose about potential share sales?

The Form 144 discloses that the Bentley 2012 Generation Skipping Trust may sell up to 300,000 Class B shares of BENTLEY SYSTEMS INC, held at Charles Schwab & Co., with an indicated aggregate market value of $11,082,000 for potential sales on or after August 27, 2026.

Who is the selling security holder in this BSY Form 144?

The selling security holder is the Bentley 2012 Generation Skipping Trust, associated with a director of BENTLEY SYSTEMS INC. The trust is filing to potentially sell Class B shares under Rule 144.

How many BSY shares are planned for sale under this Form 144?

The notice covers a proposed sale of up to 300,000 shares of BENTLEY SYSTEMS INC Class B common stock. This amount is listed in the securities information section for potential sales under Rule 144.

What is the reported market value of the BSY shares in this Form 144?

The filing lists an aggregate market value of $11,082,000 for the 300,000 Class B shares that may be sold by the Bentley 2012 Generation Skipping Trust.

How many BSY Class B shares are outstanding according to this Form 144?

The Form 144 reports 290,577,762 shares outstanding for the relevant class of BENTLEY SYSTEMS INC stock, in connection with the potential sale of 300,000 Class B shares.

How and when were the BSY shares to be sold originally acquired?

The shares were acquired as a gift on December 21, 2012, from Raymond B. Bentley, as stated in the securities-to-be-sold section of the Form 144.

AI-generated analysis. How Rhea-AI works. Not financial advice.

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Available on EDGAR 08/27/2026 - 11:59 AM Accepted by SEC EDGAR 08/27/2026 - 11:59 AM Learn about SEC filing dates

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	0002027061
Filer CCC	XXXXXXXX
Is this a LIVE or TEST Filing?	LIVE TEST
Submission Contact Information
Name
Phone
E-Mail Address

144: Issuer Information

Name of Issuer	BENTLEY SYSTEMS INC
SEC File Number	001-39548
Address of Issuer	685 STOCKTON DRIVE EXTON PENNSYLVANIA 19341
Phone	6104585000
Name of Person for Whose Account the Securities are To Be Sold	Bentley 2012 Generation Skipping Trust
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	Director

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	Charles Schwab & Co 3000 Schwab Way westlake TX 76262	300000	11082000.00	290577762	08/27/2026	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	12/21/2012	gift	Raymond B. Bentley		08/14/1987	300000	12/21/2012	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

Nothing to Report

144: Remarks and Signature

Remarks
Date of Notice	08/27/2026
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	Raymond B. Bently Generation Skipping Trust
ATTENTION: Intentional misstatements or omission of facts constitute Federal Criminal Violations (See 18 U.S.C. 1001)