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Keith A. Bentley and Barry J. Bentley founded Bentley Systems in 1984. In an interview with trade publication Geo Week News, Keith Bentley recounted how he had previously developed CAD software while working as a programmer at DuPont. After retaining rights to this software, he joined his brother Barry's chemistry software startup, and they later pivoted to the CAD software market. Their brothers Greg, Scott, and Ray later joined the company, which relocated to Pennsylvania. They introduced the commercial version of PseudoStation in 1985, which allowed users of Intergraph 's VAX systems to use low-cost graphics terminals to view and modify the designs on their Intergraph IGDS (Interactive Graphics Design System) installations. An MS-DOS version of MicroStation was introduced in 1986.
In April 2002, Bentley filed for an initial public offering, but it was withdrawn before taking effect. In November 2016, German-based Siemens announced it would pay about $76 million for a minority stake in Bentley, as well as invest in developing joint software with it.
In September 2020, Bentley Systems set terms of its IPO valuing the company at about $4.96 billion. The company would offer 10.75 million shares priced between $17 and $19 per share.
In 2023, the company reported that its annual 2022 revenue exceeded $1 billion.
Also in 2023, Keith Bentley retired from his Chief Technology role, and Greg Bentley retired in March 2024. In July 2024, Chief Operating Officer Nicholas Cumins became the first non-family member to lead the company as CEO.