08265TAD1

Bentley Systems, Incorporated

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A maker of infrastructure engineering software, Bentley Systems builds the tools used to design, build, and operate roads, bridges, water systems, power grids, and other public works, with products like MicroStation and the iTwin Platform for digital twins, plus subsurface specialist Seequent. The company was founded in 1984 by brothers Keith and Barry Bentley, who began by writing software that let engineers do CAD work on cheap desktop terminals instead of costly mainframes. Fun fact: the name comes from the Bentley brothers themselves—Keith, Barry, and several siblings all worked at the company.

CONVERTIBLEUnderlying: BSYCUSIP: 08265TAD1TechnologyUS1 derivative reporter

0.375% Convertible Senior Notes due July 1, 2027

Ownership Activity Financials Filings

Insiders

Ranked by how much each holding moved in the last year

Insider

Bentley Keith A.Director, 10% owner · 6 transactions

29.33M—

Granted 4.2K

Bentley Raymond B.Director, 10% owner · 7 transactions

15.03M—

Granted 6.9K

Bentley Barry J.Director, 10% owner · 6 transactions

11.93M-0.9%

Granted 15

Bentley Gregory SExecutive Chair & President, Director, 10% owner · 15 transactions

7.78M+0.5%

Granted 142.8K · Sold 37.3K

Shaman David R.Chief Legal Officer · 14 transactions

1.02M+0.9%

Granted 39.2K

Cumins NicholasChief Executive Officer, Director · 11 transactions

532.7K+21.2%

Granted 129.9K

Griswold Kirk B.Director · 5 transactions

468.1K+1.5%

Granted 7.1K

Andre WernerChief Financial Officer · 10 transactions

377.2K+7.6%

Granted 43.2K

Lee James KChief Operating Officer · 10 transactions

221.4K+28.7%

Granted 62.6K

Ballard BrockChief Revenue Officer · 11 transactions

94.0K+38%

Granted 37.6K

Moutte JulienChief Technology Officer · 10 transactions

90.4K+31.9%

Granted 38.2K

Hughes Brian F.Director · 1 transaction

40.5K+20%

Granted 6.7K

Haugen Janet BrutscheaDirector · 1 transaction

35.2K+23.7%

Granted 6.7K

Trimback Thomas FChief Accounting Officer · 12 transactions

19.4K+34.3%

Granted 7.7K · Sold 560

Insider	Stake change	Holds now	Granted / vested	Bought	Sold
Bentley Keith A.Director, 10% owner · 6 transactions	—	29.33M	4.2K	—	—
Bentley Raymond B.Director, 10% owner · 7 transactions	—	15.03M	6.9K	—	—
Bentley Barry J.Director, 10% owner · 6 transactions	-0.9%	11.93M	15	—	—
Bentley Gregory SExecutive Chair & President, Director, 10% owner · 15 transactions	+0.5%	7.78M	142.8K	—	37.3K
Shaman David R.Chief Legal Officer · 14 transactions	+0.9%	1.02M	39.2K	—	—
Cumins NicholasChief Executive Officer, Director · 11 transactions	+21.2%	532.7K	129.9K	—	—
Griswold Kirk B.Director · 5 transactions	+1.5%	468.1K	7.1K	—	—
Andre WernerChief Financial Officer · 10 transactions	+7.6%	377.2K	43.2K	—	—
Lee James KChief Operating Officer · 10 transactions	+28.7%	221.4K	62.6K	—	—
Ballard BrockChief Revenue Officer · 11 transactions	+38%	94.0K	37.6K	—	—
Moutte JulienChief Technology Officer · 10 transactions	+31.9%	90.4K	38.2K	—	—
Hughes Brian F.Director · 1 transaction	+20%	40.5K	6.7K	—	—
Haugen Janet BrutscheaDirector · 1 transaction	+23.7%	35.2K	6.7K	—	—
Trimback Thomas FChief Accounting Officer · 12 transactions	+34.3%	19.4K	7.7K	—	560

Select a row to see that insider’s individual transactions. Sum of the holdings confirmed in the 12 months before this insider's last filing. A Form 4 reports a holding per line — held directly, or through a named trust, partnership or foundation, and in each share class separately — never a person’s total. Lines not restated in that time are left out and shown apart: an active filer restates what they still hold, so a line they did not restate is more often an entity since renamed, whose shares a successor line reports too. An amber marker means some were left out.