[5] In 1983, Cunningham moved to Silicon Valley, where she joined Regis McKenna and worked with Steve Jobs as a project lead on the launch of the Apple Macintosh.

[8][9] She continued to work with Apple as a client, helping them launch the desktop publishing category with Aldus Corporation and Adobe Systems.

[15] Her firm's work included launching RISC microprocessors for consumer personal computers with IBM and Motorola,[16][17] very light jets with Eclipse Aviation,[18] digital imaging with Kodak, and software-as-a-service with Hewlett-Packard.

Clients included AMD, Beautiful!, Cisco, Eclipse Aviation, Futuremark, Liveops, MarketTools, PivotPoint Capital, PRTM, RSA, UCSF, VantagePoint Venture Partners, and XOJet.

[23] After leaving Rearden Commerce in the fall of 2011, Cunningham advised the Bite Communications executive team on a turnaround in North America.

[30] She led the team that spearheaded the shift in positioning from collaboration to engagement, with an initial focus on Silicon Valley as a catalyst to revitalize awareness of Avaya to the broader tech audience.

Cunningham's past board positions include RhythmOne (advertising technology), Finelite, Inc. (lighting design), YPO, CEO, Peninsula Open Space Trust (POST) and the Computer History Museum.