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Randy is a pioneering Insurance technology veteran entrepreneur and veteran Silicon Valley executive. His experience draws upon over thirty years of experience leading the design, development, and implementation of technology solutions to clients in a variety of vertical industries. Most recently, he was General Manager of Kenandy Software, a Rootstock Software company, the leading provider of cloud ERP applications utilizing the Salesforce platform.

In 1994, he founded Valley Oak Systems that became the fastest growing national provider of Claims and Risk Management solutions to the insurance industry. Valley Oak Systems was on the Inc. 500 and 5000 lists of fastest-growing private companies in America delivering their flagship product iVOS to the insurance industry.

While at Valley Oak Systems, Wheeler was a recipient of the prestigious Ernst & Young Entrepreneur of the Year® 2004 award in the “Realizing Business Potential” category.

Prior to Valley Oak Systems, Wheeler held key positions at Marathon Systems, Saddlebrook, and GRiD Systems. While at GRiD Systems, Wheeler led the group supporting the President of the United States through the White House Communications Agency (WHCA). The WHCA used over 300 portable GRiD computers and custom applications to provide all computer and communications services used by the Presidential staff during worldwide travel.