Powersteering (previously known as Cambridge Interactive) was a provider of cloud-based enterprise work management software. In 2012 the company was absorbed by Upland Software.

PowerSteering Software was founded in 1998, an outgrowth of an earlier incarnation named Cambridge Interactive, which was founded in 1994. The founder of the original company was Andrew Singleton. The original software was built to provide step-by-step instruction templates via the Internet. In 1998 David Boghossian joined the company to help found PowerSteering, and served as the company's president. The company transitioned away from services to project and portfolio management software.

PowerSteering Software was launched as a SaaS enterprise project and portfolio management (PPM) software. PowerSteering is user-configurable software, and eventually became cloud-based. The software was able to bring up management reports covering all projects under a supervisor's purview, in order for them to see what aspects of each project were on or off track. By 2005 the software was in use by over 100,000 corporate projects.

In terms of financing, in 1999 PowerSteering raised $1.3 million in angel capital, with an additional $2 million in venture capital coming in 2001. In 2002 PowerSteering raised $1 million in financing from investors, bringing its overall total in investment dollars to $4.3 million. Then in both 2003 and 2005 the company raised another $5 million in capital from investors. In 2008 the company received $3.5 million in financing from a group of investors. In 2012 PowerSteering Software was acquired by the Silverback Enterprise Group and renamed Upland Software.

Upland Software is headquartered in Austin, Texas. The CEO and Chairman of the company is Jack McDonald. Following the purchase, PowerSteering was merged with the company Tenrox, initially under the name of PowerSteering Software. Upland is backed by Austin Ventures. Upland Software is mentioned as a Visionary in the 2015 Gartner Magic Quadrant for Cloud-Based IT Project and Portfolio Management Services, Worldwide.