Bentley Systems Executive Chair Gregory Bentley Acquires 61,037 Shares via Bonus Pool Plan on July 23, 2026

Bonus Compensation Delivered Through Stock Acquisition

The SEC filing reveals that Bentley received equity compensation through Bentley Systems’ Bonus Pool Plan, with the stock portion delivered as 61,037 Class B common shares on July 23, 2026. This stock award represents the equity component of his bonus payment, executed at the market price of $30.12 per share on the distribution date. This approach aligns Bentley’s financial interests with shareholder value creation, a common practice in executive compensation within technology and software sectors.

Additionally, 26,698 shares were withheld by the company to cover Bentley’s tax withholding obligations related to the bonus. This tax withholding via share surrender ensures Bentley receives the intended net bonus benefit while the company manages the associated tax liability. Following these transactions, Bentley’s direct beneficial ownership increased to about 7.69 million Class B shares.

Bentley’s Diversified Ownership Structure

Bentley’s ownership extends beyond direct holdings to include indirect beneficial ownership. The filing discloses 29,155 shares held by his spouse and 92,654 shares beneficially owned through a 401(k) retirement plan. These indirect holdings reflect a multi-generational wealth strategy and participation in standard employee retirement benefits, even at the executive level. Combined, these holdings emphasize Bentley’s long-term investment commitment to Bentley Systems’ growth and success.

Under Section 16 beneficial ownership rules, these indirect holdings are separately reported to provide investors with a comprehensive view of executive financial stakes. This transparency helps illustrate the alignment between management and shareholders across all ownership levels.

Executive Leadership and Significant Ownership Stake

Gregory Bentley holds multiple key roles at Bentley Systems, including Director, Executive Chair, President, and beneficial owner of at least 10% of the company’s outstanding shares. These overlapping roles position him as a central figure in governance, strategic planning, and operational management. His 10% ownership stake represents a significant financial interest that aligns his wealth with the company’s long-term performance, reinforcing shareholder alignment.

As both a Director and Executive Chair, Bentley exercises board oversight and executive management responsibilities, consolidating substantial authority and decision-making power. This concentration of ownership and leadership is a critical factor for investors assessing corporate governance and executive incentive alignment. Following this transaction, Bentley’s total beneficial ownership across direct and indirect channels is approximately 7.8 million shares, underscoring his ongoing commitment as a principal stakeholder.

Transaction Execution and Regulatory Compliance

The share acquisition occurred on July 23, 2026, with the SEC Form 4 filing submitted on July 27, 2026, adhering to the four-business-day reporting requirement under Section 16 of the Securities Exchange Act. The filing was signed by Michael T. Fischette, Attorney-in-Fact for Bentley, ensuring proper legal representation and compliance with federal securities laws. This transparency allows public access to the transaction details via the SEC’s EDGAR database.

The filing details both non-derivative securities (Class B common stock acquired and withheld) and derivative securities holdings, though no derivative transactions were reported in connection with this bonus. The structured Form 4 format enables precise tracking of executive ownership changes, supporting market transparency and regulatory oversight.

Class B Common Stock Voting and Control Implications

All shares acquired are Class B common stock, which may carry distinct voting rights or economic terms compared to other classes of Bentley Systems stock. While the filing does not specify these rights, investors should consult the company’s charter documents or latest proxy statement to understand the implications of Bentley’s substantial Class B holdings on corporate control.

The concentration of Class B shares in Bentley’s hands, combined with his executive and director roles, establishes a layered control structure. If Class B shares confer enhanced voting power or economic benefits, Bentley’s 7.69 million direct shares could grant him significantly greater influence over company decisions than his equity percentage alone suggests. Investors should review Bentley Systems’ governance and capital structure disclosures for a full assessment.

Market Valuation Context

The $30.12 per share price reflects the market valuation of Bentley Systems’ Class B stock on July 23, 2026, serving as an indicator of the company’s equity value at the time of the bonus payment. This price point is relevant for investors monitoring stock performance and valuation trends. The filing does not clarify whether this price represented a premium, discount, or fair market value relative to trading activity or equity compensation practices on that date.

Investors interested in the company’s valuation methodology and executive compensation pricing may refer to quarterly financial reports, proxy statements, and management disclosures for further context.

Regulatory Oversight and Insider Trading Compliance

Form 4 filings like this one are essential to the SEC’s insider trading monitoring system, requiring officers, directors, and beneficial owners of over 10% equity to disclose ownership changes within four business days. This timely reporting enhances market transparency and helps regulators detect potential insider trading violations. No Rule 10b5-1 trading plan was indicated for this transaction, confirming it followed standard compensation procedures rather than a pre-arranged trading schedule.

The filing includes a statutory warning regarding the legal consequences of intentional misstatements or omissions under federal law. The involvement of Attorney-in-Fact Fischette underscores the engagement of professional legal counsel to ensure compliance with these requirements.

Impact on Shareholder Value and Executive Incentives

Delivering bonus compensation as company stock demonstrates Bentley Systems’ strategy to align executive rewards with shareholder returns. Equity-based compensation incentivizes executives to focus on long-term share price growth and shareholder value preservation. Bentley’s acquisition of over 61,000 shares via the bonus pool further strengthens his substantial stake in the company’s success.

However, the concentration of ownership and executive authority in one individual may raise governance considerations. Investors should evaluate whether Bentley Systems’ board includes sufficient independent oversight and accountability mechanisms to protect minority shareholders and ensure balanced decision-making.

Ongoing Ownership Reporting and Regulatory Requirements

As Bentley maintains beneficial ownership exceeding 10%, he remains subject to continuous Section 16 reporting obligations. Future acquisitions, dispositions, or ownership changes must be disclosed on Form 4 filings within four business days. Market participants can monitor these filings to identify insider trading patterns that may indicate confidence or concerns about the company’s outlook.

Additionally, Section 16(b) prohibits short-swing profit retention by executives, requiring the return of profits from trades within six months. Although this transaction was a compensatory stock award rather than an open-market trade, Bentley’s ownership activities remain governed by these regulatory frameworks, which shape executive behavior at Bentley Systems.