SEC Form DEFA14A filed by Bentley Systems Incorporated

Step 1: Go to www.envisionreports.com/BSY. Step 2: Click on Cast Your Vote or Request Materials. Step 3: Follow the instructions on the screen to log in. www.envisionreports.com/BSY Online Go to www.envisionreports.com/BSY or scan the QR code — login details are located in the shaded bar below. Stockholder Meeting Notice 043ZAD Important Notice Regarding the Availability of Proxy Materials for the Bentley Systems, Incorporated Stockholder Meeting to be Held on May 22, 2025 Under Securities and Exchange Commission rules, you are receiving this notice that the proxy materials for the annual stockholders’ meeting are available on the Internet. Follow the instructions below to view the materials and vote online or request a copy. The items to be voted on and location of the annual meeting are on the reverse side. Your vote is important! This communication presents only an overview of the more complete proxy materials that are available to you on the Internet. We encourage you to access and review all of the important information contained in the proxy materials before voting. The proxy statement and annual report to stockholders are available at: Obtaining a Copy of the Proxy Materials – If you want to receive a copy of the proxy materials, you must request one. There is no charge to you for requesting a copy. Please make your request as instructed on the reverse side on or before May 11, 2025 to facilitate timely delivery. 2NOT Easy Online Access — View your proxy materials and vote. When you go online, you can also help the environment by consenting to receive electronic delivery of future materials. The Sample Company Step 4: Make your selections as instructed on each screen for your delivery preferences. Step 5: Vote your shares. Votes submitted electronically must be received by 11:59 P.M., Eastern Time, on May 21, 2025.

Here’s how to order a copy of the proxy materials and select delivery preferences: Current and future delivery requests can be submitted using the options below. If you request an email copy, you will receive an email with a link to the current meeting materials. PLEASE NOTE: You must use the number in the shaded bar on the reverse side when requesting a copy of the proxy materials. — Internet – Go to www.envisionreports.com/BSY. Click Cast Your Vote or Request Materials. — Phone – Call us free of charge at 1-866-641-4276. — Email – Send an email to [email protected] with “Proxy Materials Bentley Systems, Incorporated” in the subject line. Include your full name and address, plus the number located in the shaded bar on the reverse side, and state that you want a paper copy of the meeting materials. To facilitate timely delivery, all requests for a paper copy of proxy materials must be received by May 11, 2025. The 2025 Annual Meeting of Stockholders of Bentley Systems, Incorporated will be held on Thursday, May 22, 2025, 11:00 A.M. Eastern time, virtually via the internet at meetnow.global/BSY2025. To access the virtual meeting, you must have the information that is printed in the shaded bar located on the reverse side of this form. Proposals to be voted on at the meeting are listed below along with the Board of Directors’ recommendations. The Board of Directors recommend a vote FOR all the nominees listed and FOR Proposals 2 and 3: 1. Election of Directors: 01 – Barry J. Bentley 02 – Gregory S. Bentley 03 – Keith A. Bentley 04 – Raymond B. Bentley 05 – Nicholas H. Cumins 06 – Kirk B. Griswold 07 – Janet B. Haugen 08 – Brian F. Hughes 2. To approve, on an advisory (non-binding) basis, the compensation paid to the Company’s named executive officers 3. To ratify the appointment of KPMG LLP as the Company’s independent registered public accounting firm for the fiscal year ending December 31, 2025 PLEASE NOTE – YOU CANNOT VOTE BY RETURNING THIS NOTICE. To vote your shares you must go online or request a paper copy of the proxy materials to receive a proxy card. Stockholder Meeting Notice