As a Managing Director, Jason is an active investor in Smart Software for the enterprise. A company builder who played an integral role in the development of one of today’s largest online businesses,, Jason acts as a thought partner, advocate, and counselor to entrepreneurs looking to take their companies from initial proof of product-market fit to industry category leadership.

Jason’s background as an operator at was very useful to our business. He gave us insight into the behavior and psyche of IT executives that other VCs do not have. He also brought with him connections to other potential customers.
—Jayaram Bhat, Founding CEO, Zenprise

Jason led the firm’s investments in and currently serves on the Boards of: Zuora (NYSE: ZUO), a SaaS-subscription billing company; Nextdoor, the world’s leading social network for neighborhoods; LeanPlum, a mobile marketing platform, Smule, a social network built around music, and ValiMail, the leader in email authentication. Jason also led the firm’s investments in companies such as Adometry (acquired by Google), Demdex (acquired by Adobe), Glint (acquired by LinkedIn), Steelbrick (acquired by Salesforce), and StrongLoop (acquired by IBM), among others.

Prior to joining Shasta in 2005, Jason was vice president, Strategy and Operations at, where he took the online retailer from zero to large scale revenue in five years. His experience growing the business into one of the largest retailers online informs his understanding of how to thoughtfully scale fast-growing businesses and use software to improve operations. Previously, Jason worked as an investment banker to venture-backed companies at Alex.Brown.

Jason earned an M.B.A. degree from Stanford Graduate School of Business and a B.S. degree in Finance from University of Maryland. He is an avid scuba diver and a passionate supporter of shark conservation.

The Twenty Minute VC: Jason Pressman

It’s time for the internet to block fake emails