Jim Kaskade

Serial Entrepreneur and Global Enterprise Executive Former Chief Executive Officer, Conversica

Last Reviewed: September 18, 2026

Executive Summary

Jim Kaskade is a technology chief executive whose career spans nearly four decades and an unusually wide range of the industry, beginning as an engineer at NCR and Teradata during the birth of enterprise data warehousing and running through semiconductor packaging, video software, cloud infrastructure, big data, consumer identity, and finally conversational AI. The consistent shape of the work has been taking a company with strong technology and an unproven commercial position and either scaling it or selling it: he grew Infochimps from nothing to fifty million dollars of revenue in two and a half years before CSC acquired it, and he led Janrain, one of the originators of consumer identity and access management, into Akamai. From October 2019 until 2025 he was Chief Executive Officer of Conversica, the private-equity-backed conversational AI company, a tenure that spanned the transition of the whole category from scripted assistants to large language models. He is an engineer by training with eight patents to his name, and he is not currently listed as an officer of an operating company.

Career Highlights

• Chief Executive Officer of Conversica from October 2019 to 2025, leading the conversational AI company through the arrival of large language models in its core market.
• Chief Executive Officer of Janrain, a pioneer of consumer identity and access management, through its acquisition by Akamai in early 2019.
• Grew Infochimps from zero to fifty million dollars of revenue in two and a half years as Chairman and Chief Executive Officer, ahead of its acquisition by CSC.
• Vice President and General Manager of Digital Applications at CSC, running a business unit of more than one billion dollars in revenue with over 7,000 employees.
• Entrepreneur in Residence at PARC, the Xerox research centre, and Senior Vice President and General Manager for cloud at SIOS Technology.
• Chief Executive Officer of Eyespot Video Network, a video software-as-a-service platform, and earlier of INCEP Technologies, a semiconductor packaging company.
• Ten years at NCR and Teradata during the formative era of enterprise data warehousing and analytics.
• Holds eight patents spanning digital phase-locked loops, processor power delivery, thermal management, metadata systems, and video editing technology.

Professional Journey

Kaskade trained as an electrical engineer at the University of California, Santa Barbara, specialising in semiconductor design and computer architecture, and joined NCR in 1988. The decade he spent there and at Teradata put him inside enterprise data warehousing at the moment it was being invented, which is the foundation for a great deal of what he did later; he also took an MBA at the University of San Diego during this period, adding finance and new product development to the engineering.

He moved into company leadership in 1999 as Chief Executive Officer of INCEP Technologies, a semiconductor packaging business working on processor power delivery and thermal management, the subject of several of his patents. From 2005 to 2008 he ran Eyespot Video Network, an early video software-as-a-service platform, which is where the video editing patents come from. A period as Senior Vice President and General Manager for cloud at SIOS Technology followed from 2009, and then a year as Entrepreneur in Residence at PARC, the Xerox research centre, from 2011.

In 2012 he became Chairman and Chief Executive Officer of Infochimps, a big data platform company, and grew it from no revenue to fifty million dollars within two and a half years, at which point CSC acquired it. He stayed with the acquirer and stepped up in scale considerably, becoming Vice President and General Manager of Digital Applications, a business unit carrying more than a billion dollars of revenue and over seven thousand people. It was the one stretch of his career spent running a large division of a very large company rather than a whole small one.

He returned to venture-scale leadership as Chief Executive Officer of Janrain, which had effectively created the consumer identity and access management category: the infrastructure behind social login, consent, and customer profile management. Under his leadership the company was positioned and sold to Akamai in early 2019, giving the content delivery giant an identity layer.

In October 2019 he took over as Chief Executive Officer of Conversica, succeeding Alex Terry. Conversica sold AI assistants that pursued sales and marketing leads through email and messaging conversations, a category it had largely defined, and Kaskade’s tenure coincided with the most disruptive possible development for that business: the arrival of large language models, which simultaneously validated the premise of conversational revenue automation and destroyed the technical moat around doing it with hand-built dialogue systems. He led the company through that transition until 2025, when he departed and Michael Gilson was appointed chief executive.

Since leaving Conversica he has described himself simply as a serial entrepreneur and global enterprise executive, without naming a current operating role. Outside the corporate track he co-founded the sustainable clothing ventures GreenEdge Kids and GreenEdge Denim with his wife Annie, mentors early-stage founders through the Founder Institute, and writes prolifically on AI and enterprise technology.

Education

University of California, Santa Barbara

BS, Electrical Engineering and Computer Science (1984-1988), concentrating on semiconductor design and computer architecture

University of San Diego

MBA (1989-1993), concentrating on finance, entrepreneurship, and new product development