The most recent Bentley Systems (BSY) insider transaction: Raymond B. Bentley (Director, TenPercentOwner) sold 344,203 shares worth about $13.85Mn on Oct 30, 2026, reported on Form 4 on Nov 3, 2026. So far in the quarter ending Dec 31, 2026, insiders were net sellers of 464.18K shares.
Over the past year, BSY insiders sold $20.12 million of stock (500.66K shares) on the open market and bought none.
| # | Insider | Position | Direct | Indirect | Total | Share of Insiders | Last Filed |
|---|---|---|---|---|---|---|---|
| 1 | Raymond B. Bentley | Executive Vice President | 14,316,404 | 0 | 14,316,404 | 33.1% | 03 Nov, 2026 |
| 2 | Barry J. Bentley | Director, TenPercentOwner | 11,837,896 | 0 | 11,837,896 | 27.4% | 01 Oct, 2026 |
| 3 | Gregory S Bentley | Executive Chair President | 7,716,252 | 0 | 7,716,252 | 17.9% | 26 Oct, 2026 |
| 4 | Keith A. Bentley | Chief Technology Officer | 3,845,254 | 0 | 3,845,254 | 8.9% | 01 Oct, 2026 |
| 5 | David J. Hollister | Chief Investment Officer | 1,964,392 | 0 | 1,964,392 | 4.5% | 09 Mar, 2023 |
| 6 | Gus Bergsma | Chief Revenue Officer | 874,899 | 0 | 874,899 | 2.0% | 26 Jan, 2023 |
| 7 | David R. Shaman | Chief Legal Officer | 622,995 | 0 | 622,995 | 1.4% | 01 Oct, 2026 |
| 8 | Nicholas Cumins | Chief Executive Officer | 533,221 | 0 | 533,221 | 1.2% | 01 Oct, 2026 |
| 9 | Kirk B. Griswold | Director | 468,202 | 0 | 468,202 | 1.1% | 01 Oct, 2026 |
| 10 | Werner Andre | Chief Financial Officer | 377,843 | 0 | 377,843 | 0.9% | 01 Oct, 2026 |
| 11 | James K Lee | Chief Operating Officer | 221,712 | 0 | 221,712 | 0.5% | 01 Oct, 2026 |
| 12 | Brock Ballard | Chief Revenue Officer | 94,037 | 0 | 94,037 | 0.2% | 15 Jun, 2026 |
| 13 | Julien Moutte | Chief Technology Officer | 90,862 | 0 | 90,862 | 0.2% | 01 Oct, 2026 |
| 14 | Andrew Rahden | Chief Revenue Officer | 88,319 | 0 | 88,319 | 0.2% | 01 Oct, 2026 |
| 15 | Michael M Campbell | Chief Product Officer | 70,186 | 0 | 70,186 | 0.2% | 16 Dec, 2024 |
| 16 | Brian F. Hughes | Director | 40,500 | 0 | 40,500 | 0.1% | 26 May, 2026 |
| 17 | Janet Brutschea Haugen | Director | 35,198 | 0 | 35,198 | 0.1% | 26 May, 2026 |
| 18 | Thomas F Trimback | Chief Accounting Officer | 19,292 | 0 | 19,292 | 0.0% | 27 Oct, 2026 |
Each row is that insider’s most recently reported position, from Form 4 filings over the last 60 months — which is why this total does not tie to the quarterly series above, where a quarter counts only the insiders who filed in it. Shares held through a fund or institutional portfolio are counted on the institutional ownership page instead.
| Date | Insider | Position | Transaction | Shares | Price | Value | Shares Held After | Ownership |
|---|---|---|---|---|---|---|---|---|
| 30 Oct, 2026 | Raymond B. Bentley | Director, TenPercentOwner | Disposed S | 344,203 | $40.24 | $13.85Mn | 14,316,404 | Direct |
| 25 Oct, 2026 | Thomas F Trimback | Chief Accounting Officer | Disposed F | 74 | $39.70 | $2.94K | 19,292 | Direct |
| 23 Oct, 2026 | Raymond B. Bentley | Director, TenPercentOwner | Disposed S | 16,662 | $40.00 | $666.49K | 14,799,742 | Direct |
| 26 Oct, 2026 | Raymond B. Bentley | Director, TenPercentOwner | Disposed S | 139,135 | $40.05 | $5.57Mn | 14,660,607 | Direct |
| 22 Oct, 2026 | Gregory S Bentley | Executive Chair President | Acquired A | 63,793 | $39.41 | $2.51Mn | 7,744,155 | Direct |
| 22 Oct, 2026 | Gregory S Bentley | Executive Chair President | Disposed F | 27,903 | $39.41 | $1.10Mn | 7,716,252 | Direct |
| 29 Sep, 2026 | Barry J. Bentley | Director, TenPercentOwner | Acquired A | 3 | $0.00 | $0 | 11,837,896 | Direct |
| 29 Sep, 2026 | Andrew Rahden | Chief Revenue Officer | Acquired A | 174 | $0.00 | $0 | 88,319 | Direct |
| 29 Sep, 2026 | James K Lee | Chief Operating Officer | Acquired A | 402 | $0.00 | $0 | 221,712 | Direct |
| 29 Sep, 2026 | Julien Moutte | Chief Technology Officer | Acquired A | 106 | $0.00 | $0 | 90,862 | Direct |
| 29 Sep, 2026 | Thomas F Trimback | Chief Accounting Officer | Acquired A | 23 | $0.00 | $0 | 19,366 | Direct |
| 29 Sep, 2026 | Gregory S Bentley | Executive Chair President | Acquired A | 3,691 | $0.00 | $0 | 7,680,362 | Direct |
| 29 Sep, 2026 | Keith A. Bentley | Director, TenPercentOwner | Acquired A | 1,033 | $0.00 | $0 | 3,845,254 | Direct |
| 29 Sep, 2026 | David R. Shaman | Chief Legal Officer | Acquired A | 469 | $0.00 | $0 | 622,995 | Direct |
| 29 Sep, 2026 | Nicholas Cumins | Chief Executive Officer | Acquired A | 737 | $0.00 | $0 | 533,221 | Direct |
| 29 Sep, 2026 | Werner Andre | Chief Financial Officer | Acquired A | 199 | $0.00 | $0 | 377,843 | Direct |
| 29 Sep, 2026 | Kirk B. Griswold | Director | Acquired A | 85 | $0.00 | $0 | 468,202 | Direct |
| 29 Sep, 2026 | Raymond B. Bentley | Director, TenPercentOwner | Acquired A | 2,044 | $0.00 | $0 | 14,816,404 | Direct |
| 31 Aug, 2026 | David R. Shaman | Chief Legal Officer | Disposed F | 6,665 | $36.75 | $244.94K | 622,681 | Direct |
| 27 Aug, 2026 | Gregory S Bentley | Executive Chair President | Disposed G | 13,192 | $0.00 | $0 | 7,676,671 | Direct |