Maynard is the founder of the Webb Investment Network (WIN), a seed investment firm. He is a co-founder and board member of Everwise, a talent development startup, and a board member of Visa and Salesforce. Previously, Maynard served as Chairman of the Board of Yahoo!, CEO of LiveOps, COO of eBay, and held executive roles at Gateway, Bay Networks, and Quantum. He started his career at IBM, where he spent 11 years in a variety of roles in security, finance and IT.