According to recent filings covering the 90 days ending January 10, 2026, the three most significant insider holders at Bentley Systems are TenPercentOwner Invest Management Sarl Spt (24.87Mn shares), Director Raymond B. Bentley (15.10Mn shares), Director Barry J. Bentley (11.84Mn shares).
| Holder | Position | Shares | Report Date |
|---|---|---|---|
| Invest Management Sarl Spt | 24,869,645 | 07 Jul, 2021 | |
| Raymond B. Bentley | 15,103,583 | 15 Dec, 2025 | |
| Barry J. Bentley | 11,837,887 | 05 Jan, 2026 | |
| Gregory S Bentley | Executive Chair & President | 7,624,756 | 15 Dec, 2025 |
| Keith A. Bentley | 3,937,010 | 05 Jan, 2026 | |
| David J. Hollister | Chief Investment Officer | 1,964,392 | 09 Mar, 2023 |
| David R. Shaman | Chief Legal Officer | 912,063 | 17 Dec, 2025 |
| Gus Bergsma | See Remarks | 874,899 | 26 Jan, 2023 |
| Kirk B. Griswold | 461,212 | 15 Dec, 2025 | |
| Richard P. Bentley | 459,278 | 16 Jun, 2021 | |
| Nicholas Cumins | Chief Executive Officer | 423,112 | 17 Dec, 2025 |
| Werner Andre | Chief Financial Officer | 346,962 | 17 Dec, 2025 |
| James K Lee | Chief Operating Officer | 163,290 | 17 Dec, 2025 |
| Michael M Campbell | Chief Product Officer | 70,186 | 16 Dec, 2024 |
| Julien Moutte | Chief Technology Officer | 68,975 | 15 Dec, 2025 |
| Brock Ballard | Chief Revenue Officer | 65,977 | 05 Jan, 2026 |
| Brian F. Hughes | 33,751 | 27 May, 2025 | |
| Janet Brutschea Haugen | 28,449 | 27 May, 2025 | |
| Thomas F Trimback | Chief Accounting Officer | 13,822 | 15 Dec, 2025 |
* Please note that the shares above only reflect shares from the fund portfolio and the institutional portfolio. Shares from the personal portfolio are excluded from this Institutional Ownership Page. See these insiders' latest transactions here on Insider Page.
| Transaction Date | Insider Name | Security Class | Transaction Type | Shares Traded | Price | Shares Remaining | Ownership | Code |
|---|---|---|---|---|---|---|---|---|
| 01 Jan, 2026 | Keith A. Bentley | Class B Common Stock | D | 24,625 | $38.16 | 3,937,010 | D | F |
| 01 Jan, 2026 | Barry J. Bentley | Class B Common Stock | D | 371 | $38.16 | 11,837,887 | D | F |
| 01 Jan, 2026 | Brock Ballard | Class B Common Stock | D | 2,223 | $38.16 | 65,977 | D | F |
| 15 Dec, 2025 | David R. Shaman | Class B Common Stock | D | 730 | $40.25 | 635,255 | D | F |
| 15 Dec, 2025 | David R. Shaman | - | - | 635,255 | D | |||
| 15 Dec, 2025 | David R. Shaman | Class B Common Stock | D | 4,165 | $40.25 | 635,985 | D | F |
| 15 Dec, 2025 | David R. Shaman | Class B Common Stock | D | 2,500 | $0.00 | 632,755 | D | G |
| 15 Dec, 2025 | David R. Shaman | - | - | 632,755 | D | |||
| 15 Dec, 2025 | Werner Andre | Class B Common Stock | D | 4,401 | $40.25 | 346,962 | D | F |
| 15 Dec, 2025 | Nicholas Cumins | - | - | 423,112 | D | |||
| 15 Dec, 2025 | Nicholas Cumins | Class B Common Stock | D | 17,162 | $40.25 | 423,112 | D | F |
| 15 Dec, 2025 | James K Lee | Class B Common Stock | D | 9,166 | $40.25 | 163,290 | D | F |
| 11 Dec, 2025 | Gregory S Bentley | Class B Common Stock | A | 3,958 | $0.00 | 7,595,601 | D | A |
| 11 Dec, 2025 | Keith A. Bentley | Class B Common Stock | A | 1,284 | $0.00 | 3,961,635 | D | A |
| 11 Dec, 2025 | Barry J. Bentley | Class B Common Stock | A | 5 | $0.00 | 11,838,258 | D | A |
| 11 Dec, 2025 | David R. Shaman | Class B Common Stock | A | 460 | $0.00 | 640,150 | D | A |
| 11 Dec, 2025 | Raymond B. Bentley | Class B Common Stock | A | 1,730 | $0.00 | 15,103,583 | D | A |
| 11 Dec, 2025 | Kirk B. Griswold | Class B Common Stock | A | 85 | $0.00 | 461,212 | D | A |
| 11 Dec, 2025 | Werner Andre | - | - | 351,363 | D | |||
| 11 Dec, 2025 | Werner Andre | Class B Common Stock | A | 157 | $0.00 | 351,363 | D | A |