Bentley Systems's three largest insider shareholders as of September 23, 2026 are Raymond B. Bentley (Executive Vice President, 14.81Mn shares), Barry J. Bentley (Director, 11.84Mn shares), Gregory S Bentley (Executive Chair President, 7.68Mn shares).
| # | Insider | Position | Direct | Indirect | Total | Share of Insiders | Last Filed |
|---|---|---|---|---|---|---|---|
| 1 | Raymond B. Bentley | Executive Vice President | 14,814,360 | 0 | 14,814,360 | 34.0% | 15 Jun, 2026 |
| 2 | Barry J. Bentley | Director, TenPercentOwner | 11,837,893 | 0 | 11,837,893 | 27.2% | 15 Jun, 2026 |
| 3 | Gregory S Bentley | Executive Chair President | 7,676,671 | 0 | 7,676,671 | 17.6% | 31 Aug, 2026 |
| 4 | Keith A. Bentley | Chief Technology Officer | 3,844,221 | 0 | 3,844,221 | 8.8% | 15 Jun, 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 | 622,681 | 0 | 622,681 | 1.4% | 02 Sep, 2026 |
| 8 | Nicholas Cumins | Chief Executive Officer | 532,717 | 0 | 532,717 | 1.2% | 15 Jun, 2026 |
| 9 | Kirk B. Griswold | Director | 468,117 | 0 | 468,117 | 1.1% | 15 Jun, 2026 |
| 10 | Werner Andre | Chief Financial Officer | 377,169 | 0 | 377,169 | 0.9% | 15 Jun, 2026 |
| 11 | James K Lee | Chief Operating Officer | 221,414 | 0 | 221,414 | 0.5% | 15 Jun, 2026 |
| 12 | Brock Ballard | Chief Revenue Officer | 94,037 | 0 | 94,037 | 0.2% | 15 Jun, 2026 |
| 13 | Julien Moutte | Chief Technology Officer | 90,367 | 0 | 90,367 | 0.2% | 15 Jun, 2026 |
| 14 | Michael M Campbell | Chief Product Officer | 70,186 | 0 | 70,186 | 0.2% | 16 Dec, 2024 |
| 15 | Brian F. Hughes | Director | 40,500 | 0 | 40,500 | 0.1% | 26 May, 2026 |
| 16 | Janet Brutschea Haugen | Director | 35,198 | 0 | 35,198 | 0.1% | 26 May, 2026 |
| 17 | Thomas F Trimback | Chief Accounting Officer | 19,376 | 0 | 19,376 | 0.0% | 15 Jun, 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 |
|---|---|---|---|---|---|---|---|---|
| 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 |
| 12 Aug, 2026 | Gregory S Bentley | Executive Chair President | Disposed G | 703 | $0.00 | $0 | 7,690,144 | Direct |
| 12 Aug, 2026 | Gregory S Bentley | Executive Chair President | Disposed G | 281 | $0.00 | $0 | 7,689,863 | Direct |
| 02 Aug, 2026 | David R. Shaman | Chief Legal Officer | Disposed F | 1,040 | $35.68 | $37.11K | 629,346 | Direct |
| 23 Jul, 2026 | Gregory S Bentley | Executive Chair President | Acquired A | 61,037 | $30.12 | $1.84Mn | 7,717,545 | Direct |
| 23 Jul, 2026 | Gregory S Bentley | Executive Chair President | Disposed F | 26,698 | $30.12 | $804.14K | 7,690,847 | Direct |
| 08 Jul, 2026 | David R. Shaman | Chief Legal Officer | Disposed F | 704 | $31.65 | $22.28K | 629,731 | Direct |
| 11 Jun, 2026 | Keith A. Bentley | Director, TenPercentOwner | Acquired A | 1,050 | $0.00 | $0 | 3,844,221 | Direct |
| 11 Jun, 2026 | Julien Moutte | Chief Technology Officer | Acquired A | 201 | $0.00 | $0 | 90,367 | Direct |
| 11 Jun, 2026 | Brock Ballard | Chief Revenue Officer | Acquired A | 202 | $0.00 | $0 | 94,037 | Direct |
| 11 Jun, 2026 | Thomas F Trimback | Chief Accounting Officer | Acquired A | 42 | $0.00 | $0 | 19,376 | Direct |
| 11 Jun, 2026 | Barry J. Bentley | Director, TenPercentOwner | Acquired A | 3 | $0.00 | $0 | 11,837,893 | Direct |
| 11 Jun, 2026 | Gregory S Bentley | Executive Chair President | Acquired A | 3,749 | $0.00 | $0 | 7,656,508 | Direct |
| 11 Jun, 2026 | Werner Andre | Chief Financial Officer | Acquired A | 301 | $0.00 | $0 | 377,169 | Direct |
| 11 Jun, 2026 | Kirk B. Griswold | Director | Acquired A | 86 | $0.00 | $0 | 468,117 | Direct |
| 11 Jun, 2026 | Raymond B. Bentley | Director, TenPercentOwner | Acquired A | 2,076 | $0.00 | $0 | 14,814,360 | Direct |
| 11 Jun, 2026 | Nicholas Cumins | Chief Executive Officer | Acquired A | 878 | $0.00 | $0 | 532,717 | Direct |
| 11 Jun, 2026 | David R. Shaman | Chief Legal Officer | Acquired A | 620 | $0.00 | $0 | 630,435 | Direct |
| 11 Jun, 2026 | James K Lee | Chief Operating Officer | Acquired A | 466 | $0.00 | $0 | 221,414 | Direct |