BENTLEY SYSTEMS INC (BSY) — Insider Trading

AI-Powered SEC Filing Analysis

Latest Insider Trading Filed: 2026-05-05

Key Insights

Chief Legal Officer David R. Shaman executed a tax-withholding transaction on 5/3/2026, disposing of 5,287 shares at $33.58 (VWAP) as part of a Non-Qualified Deferred Compensation Plan distribution, indicating routine compensation settlement rather than discretionary selling.
Following the transaction, Shaman maintains substantial beneficial ownership of 654,288 Class B Common Stock shares directly plus 367,470 shares indirectly (via GRATs, spouse trustee, and 401(k) plan), demonstrating significant continued confidence in BSY despite the share withholding.
The transaction is non-discretionary and tax-related per Form 4 explanation, making it a neutral insider activity signal that does not reflect bearish or bullish sentiment from company leadership regarding BSY's future performance.

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Earlier Insider Trading filings

Filed: 2026-04-27

Gregory S. Bentley, Executive Chair & President, acquired 62,032 shares of Class B Common Stock at $32.65 per share on 04/23/2026 through the company's Bonus Pool Plan, representing compensation rather than open market purchases.
Bentley sold 27,133 shares to cover tax withholding obligations related to the bonus payment, a routine practice that reduced net acquisition to approximately 35,000 shares after tax withholding.
Following the transaction, Bentley's direct beneficial ownership increased to 7,652,759 Class B shares, while maintaining substantial indirect ownership through spouse holdings (29,155 shares) and 401(k) plan (92,654 shares), demonstrating significant personal investment alignment with the company.
As a 10% owner and the company's Executive Chair & President, this transaction reflects internal compensation practices rather than open market confidence signals, limiting its predictive value for broader shareholder sentiment.

Filed: 2026-04-03

The reporting person, Julien Moutte, who is the Chief Technology Officer, sold 3,007 shares of the company's Class B Common Stock on April 1, 2026, likely to cover tax obligations associated with the vesting of previously granted awards.
This transaction represents a small portion (3.2%) of the reporting person's total beneficial ownership of 90,166 shares, suggesting this may be a routine transaction rather than a significant change in their position.
The reporting of insider transactions, such as this sale, can provide investors with insights into the perspectives and actions of key company personnel, which may be informative when evaluating the company's outlook and performance.

Filed: 2026-03-31

The reporting person, Thomas F. Trimback, is the Chief Accounting Officer of Bentley Systems Inc. and has disposed of 172 Class B Common Stock shares through a transaction to cover taxes due upon the vesting of previously granted awards.
The transaction occurred on March 29, 2026, and the reporting person now beneficially owns 19,334 Class B Common Stock shares.
Insider transactions, especially those involving the disposal of shares to cover tax obligations, can provide insights into the financial situation and management incentives of the company.

Filed: 2026-03-23

The reporting person, Raymond B. Bentley, is a director and 10% owner of Bentley Systems Inc. (BSY), indicating a significant stake in the company.
Bentley acquired 1,671 shares of Class B common stock on March 19, 2026, likely through the vesting of dividend equivalent rights associated with previous equity awards.
Bentley also holds indirect beneficial ownership of 125,000 shares through his spouse and 92,654 shares through a 401(k) plan, suggesting a broader ownership position in the company.

Filed: 2026-03-23

The reporting person, Brock Ballard, acquired 163 shares of Class B common stock of Bentley Systems, Inc. (BSY) through dividend equivalent rights associated with previously granted awards.
Ballard's total beneficial ownership of BSY shares increased to 93,835 shares, demonstrating his continued commitment to the company.
This transaction was a routine equity award distribution and does not indicate any significant changes in Ballard's position or the company's outlook.

Filed: 2026-03-23

The reporting person, Barry J. Bentley, is a director and 10% owner of Bentley Systems Inc. (BSY), indicating their significant stake in the company.
Bentley acquired 3 additional shares of Class B common stock through dividend equivalent rights, further increasing their direct beneficial ownership in the company.
The reporting person also holds an indirect beneficial ownership of 92,654 shares of Class B common stock through a 401(k) plan.

Filed: 2026-03-23

The reporting person, David R. Shaman, who is the Chief Legal Officer of Bentley Systems Inc., acquired 546 shares of Class B common stock as dividend equivalent rights, indicating ongoing executive compensation and alignment with shareholder interests.
Shaman also holds a significant amount of Bentley Systems stock through indirect ownership, with 279,308 shares held in Grantor Retained Annuity Trusts, 55,527 shares held by his spouse, and 32,635 shares held through a 401(K) plan, suggesting a long-term commitment to the company.
The lack of any derivative security transactions reported suggests a focus on long-term equity ownership rather than short-term trading, which may be viewed positively by investors.

Filed: 2026-03-23

The reporting person, Andre Werner, acquired 243 shares of Class B Common Stock through dividend equivalent rights, increasing their total beneficial ownership to 376,868 shares.
This transaction represents a relatively small increase in the reporting person's stake, suggesting they are maintaining their existing position in the company.
The fact that the shares were acquired through dividend equivalent rights, rather than an open market purchase, indicates this was a routine, non-discretionary transaction.

Filed: 2026-03-23

Gregory S. Bentley, the Executive Chair and President, acquired 3,019 shares of Class B Common Stock through dividend equivalent rights, increasing his direct ownership to over 7.6 million shares.
Bentley also holds indirect ownership of 29,155 shares through his spouse and 92,654 shares through the company's 401(K) plan, indicating significant insider ownership.
The insider buying activity suggests Bentley's confidence in the company's prospects and alignment with shareholders' interests.

Filed: 2026-03-23

The reporting person, Keith A. Bentley, acquired 845 shares of Class B Common Stock, increasing his direct ownership to 3,843,171 shares.
The reporting person also holds 12,696,921 shares of Class B Common Stock indirectly through a Grantor Retained Annuity Trust, and 92,654 shares through a 401(K) plan.
The acquisition of shares appears to be related to dividend equivalent rights that accrued to the reporting person in connection with a dividend paid by the issuer on awards previously granted.

Filed: 2026-03-23

Nicholas Cumins, the Chief Executive Officer of Bentley Systems Inc., acquired 707 shares of Class B Common Stock on March 19, 2026 through dividend equivalent rights at no cost.
This transaction increased Cumins' direct beneficial ownership of Bentley Systems' shares to 531,839, indicating his continued commitment to the company.
Insider buying is generally seen as a positive signal, as it suggests the executive believes the company's stock is undervalued and has confidence in its future performance.

Filed: 2026-03-23

The reporting person, James K. Lee, who is the Chief Operating Officer of Bentley Systems Inc., acquired 375 shares of Class B Common Stock through dividend equivalent rights at $0.00 per share.
This insider transaction suggests the reporting person's continued confidence in the company and aligns their interests with shareholders.
The reporting person's total beneficial ownership of 220,948 shares indicates a significant stake in the company, potentially signaling their commitment to the long-term success of Bentley Systems.

Filed: 2026-03-23

The reporting person, Kirk B. Griswold, acquired 70 shares of the issuer's Class B Common Stock through dividend equivalent rights, indicating continued ownership and confidence in the company.
The transaction was a non-derivative security acquisition, suggesting the reporting person is maintaining or increasing their direct stake in the issuer.
The reporting person is a director of the issuer, Bentley Systems Inc., providing insight into insider sentiment and potential strategic direction.

Filed: 2026-03-23

Julien Moutte, the Chief Technology Officer of Bentley Systems Inc. (BSY), acquired 173 shares of the company's Class B common stock on March 19, 2026 at no cost, likely through a dividend equivalent rights program.
This transaction increases Moutte's direct beneficial ownership of BSY shares to 93,173, suggesting the executive has a significant stake in the company and is likely aligned with shareholder interests.
Insider purchases can signal management's confidence in the company's outlook and future performance, which could be a positive signal for investors.

Filed: 2026-03-23

The reporting person, Thomas F. Trimback, acquired 35 shares of the issuer's Class B common stock through dividend equivalent rights, increasing his direct ownership to 19,506 shares.
Insider ownership transactions like this can provide insights into management's confidence in the company's future prospects.
The timing of this transaction, which occurred on March 19, 2026, should be considered in the context of any recent company news or financial reporting.

Filed: 2026-03-19

Julien Moutte, the Chief Technology Officer of Bentley Systems Inc., sold 431 Class B common shares on March 17, 2026 at $37.88 per share.
This transaction appears to be a sell-to-cover arrangement, where shares were sold to cover tax obligations related to previously granted awards.
Moutte still holds 93,000 Class B common shares directly following the reported transaction.

Other reports for BENTLEY SYSTEMS INC

Quarterly Report Current Report

Important Information

AI-generated analysis is for informational purposes only. Always read original SEC filings and consult with qualified professionals before making investment decisions.