Bentley Systems Inc. Executive Chair & President Gregory S. Bentley acquired 3,691 shares of Class B Common Stock on September 29, 2026, as dividend equivalent rights accrued in connection with a dividend paid on previously granted awards. He held 7,680,362 shares directly after the acquisition. The filing also lists 29,155 shares held by his spouse and 92,654 shares held by a 401(k) plan.
Bentley Systems Inc. (BSY) director and 10% owner Barry J. Bentley acquired 3 shares of Class B Common Stock on September 29, 2026, representing dividend equivalent rights accrued in connection with a dividend paid on previously granted awards. The rights vest on the same terms as those awards. His reported direct holdings after the transaction were 11,837,896 shares; he also reported 92,654 shares held indirectly through the 401(k) Plan.
BENTLEY SYSTEMS INC (BSY) reported the initial equity holdings of Chief Revenue Officer Andrew Rahden on a Form 3. He beneficially owns 88,145 shares of the company’s Class B Common Stock directly, including 87,511 restricted shares of Class B Common Stock of the issuer.
Bentley Systems, Incorporated (BSY) announced that its Board of Directors declared a $0.07 per share cash dividend for the third quarter of 2026. The dividend will be payable on September 29, 2026 to stockholders of record of both Class A and Class B common stock as of the close of business on September 22, 2026.
The company notes that any future decisions regarding share repurchases or quarterly dividends will depend on its financial condition, results of operations, and other factors such as macroeconomic conditions and tax law changes, as determined by its board of directors.
BENTLEY SYSTEMS INC (BSY) reported that Chief Legal Officer David R. Shaman had 6,665 shares of Class B Common Stock withheld on August 31, 2026 to pay tax liabilities in connection with a scheduled distribution from the issuer's Non-Qualified Deferred Compensation Plan, at a reference price of $36.75 per share. Following this tax-withholding disposition, he held 622,681 Class B shares directly, plus additional indirect holdings through Grantor Retained Annuity Trusts, a spouse trustee account, and a 401(k) plan. No transactions were reported under a Rule 10b5-1 trading plan.
BENTLEY SYSTEMS INC (BSY) reported that Executive Chair & President Gregory S. Bentley made a bona fide gift of 13,192 shares of Class B Common Stock on 2026-08-27. After this gift, he directly holds 7,676,671 Class B shares, with additional indirect holdings of 29,155 shares held by his spouse and 92,654 shares held through a 401(k) plan.
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.
Bentley Systems Inc. executive Gregory S. Bentley, who serves as Executive Chair, President and a more than 10% owner, reported making bona fide gifts of Class B Common Stock on 2026-08-12. He transferred 703 shares and 281 shares at a stated price of $0.00 per share. The filing also reports indirect holdings of Class B Common Stock, including 29,155 shares held by his spouse and 92,654 shares held through a 401(K) Plan.
Bentley Systems reported for the three and six months ended June 30, 2026. Total revenues were $410,727 for the quarter and $834,908 year-to-date, increases of 12.8% and 13.6% versus 2025, driven mainly by subscriptions of $378,635 and $771,119. Annualized recurring revenues were $1,535,988 with a 12% constant-currency ARR growth rate and a last-twelve-month recurring revenues dollar-based net retention rate of 109%.
Operating income was $88,608 for the quarter and $214,868 for six months; AOI less Operating SBC was $116,036 and $256,959. Net income attributable to Bentley Systems was $78,573 for the quarter ($0.25 diluted EPS) and $173,959 for six months ($0.55 diluted EPS). Cash flows from operating activities were $264,921 compared with $280,500 a year earlier. Cash and cash equivalents were $146,981 and total debt was $1,217,180, including a new $550,000 term loan used in part to repay $678,254 at maturity of the 2026 convertible notes. The company repurchased 3,747,742 Class B shares for $125,075 and paid cash dividends of $0.14 per share, or $42,444 in total, during the first half of 2026.
Bentley Systems reported second‑quarter 2026 total revenues of $410.7 million, up 12.8% year‑over‑year (12.2% on a constant currency basis). Subscriptions revenue was $378.6 million, up 13.6%, and Annualized Recurring Revenues were $1,536.0 million with a last twelve‑month dollar‑based net retention rate of 109%.
Operating income margin for the quarter was 21.6% versus 23.2% a year earlier, while AOI less Operating SBC margin was 28.3% versus 29.3%. Net income per diluted share rose to $0.25 from $0.22, and Adjusted EPS increased to $0.35 from $0.32. Free cash flow for the quarter was $63.8 million, up from $57.0 million.
For the first six months of 2026, total revenues were $834.9 million, up 13.6% year‑over‑year, with subscriptions revenue of $771.1 million, up 14.1%. Management emphasized continued demand in resources and public works/utilities, progress in Infrastructure AI offerings, and the use of non‑GAAP metrics such as AOI less Operating SBC, Adjusted EPS, free cash flow, and Adjusted EBITDA to assess underlying performance and liquidity.