[11] In 2001, Thoughtworks agreed to settle a lawsuit by Microsoft for $480,000 for deploying unlicensed copies of office productivity software to employees.

The division created, supported and sold agile project management and software development and deployment tools including Mingle,[18] Gauge (formerly Twist), Snap CI[19] and GoCD.

[27] In April 2013, Thoughtworks announced a collective leadership structure and appointed four co-Presidents of the global organization.

[32] In 2015, Guo Xiao, who started as a developer in Thoughtworks China in 1999, became the chief executive officer and President.

[35] Singham sold the company to British private equity firm Apax Partners in 2017 for $785 million, by which time it had 4,500 employees across 15 countries, including South Africa.

[39] At the end of January 2021, Thoughtworks raised $720 million in funding according to data compiled by Chicago Inno.

[40] The following month, Thoughtworks acquired Fourkind, a machine learning and data science consulting company based in Finland.

[41] In March 2021, Thoughtworks worked with the Veterans Affairs Department to deploy a centralized mechanism for delivering updates via 'VANotify'.

[50] Translation Cards is an open source Android app that helps field workers and refugees communicate more effectively and confidently[promotion?].

With the help of Google volunteers, Mercy Corps partnered with Thoughtworks and UNHCR to create the app.