[2] The company was established in 2001 and founded by: Ken Branson, James Kwak, John Raguin, and Marcus Ryu from Ariba (and McKinsey, where James and Marcus had met); and John Seybold and Mark Shaw from Kana Software.

[10] In 2017, Guidewire acquired Cyence, a data science and risk analytics company enabling P&C insurers to grow.

[12][13] In March 2023, Guidewire executed a sublease agreement to exchange headquarters with Roblox Corporation, another software company in San Mateo.

Guidewire will move into and assume the remaining lease term for the Roblox headquarters at 970 Park Place, near the Franklin Templeton campus; Roblox will assume Guidewire's remaining lease term for Bay Meadows Station 2 at 2850 Delaware Street.

Its three main software products are ClaimCenter, PolicyCenter, and BillingCenter, each servicing a major component of a P&C insurance carrier.